Hey Girl U Up?

105| PETER PAN - THE LOST (SINGLE) BOYS!| GUESTS: NEIL BENTLEY FIERRO & DREW LEWANDOWSKI

• Anna Moulaison • Season 1 • Episode 5

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Why are so many men over 40 still single, never married, and child-free? Are they emotionally unavailable? Lovable lone wolves? Or just playing the long game?

In this episode of Hey Girl, U Up?, Anna sits down with two real-life “Lost Boys” — Neil Bentley Fierro and Drew Lewandowski — for a wide-ranging, hilarious, and at times brutally honest conversation about modern dating, commitment fears, and what it means to grow up (or not) in the era of endless swiping.

Drew is a self-proclaimed hopeless romantic with a long trail of almosts, while Neil prefers meeting women “in the wild” and dreams of a traditional cheerleader-style partner — minus the emotional labor. Together, they dive into what men really want, what turns them off, and why dating after 40 is such a minefield for both sides.

From explosive first-date disasters and ghosting regrets to the pros and cons of single moms, religious dealbreakers, and sex on the first night, this episode is packed with sharp takes, big laughs, and surprising vulnerability. We also play "Regret Roulette," roast the wildest dating bios in our weekly "Biohazard" segment, and rank red flags with “Flagged or Bagged.”

If you've ever wondered why some men never seem to settle down — or if you're dating one right now — this is the episode that pulls back the curtain. No shame, no sugarcoating.

Featuring confessions, contradictions, and just enough espresso martinis to keep it spicy, Peter Pan – The Lost (Single) Boys is a must-listen for anyone navigating the strange, funny, and often frustrating world of dating over 40.

Follow the show at heygirluup.com or on Instagram and TikTok @heygirluup. New episodes every week.

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Anna:

Hey girl, you up always. Hey girl, you up man. Boys fuck boys. Playboy boys. Do they ever grow up? Well, if I think you haven't, I'm gonna call you a Peter Pan. So that's what we call in this episode, Peter Pan, and I'll be your Wendy. Now let's meet some lost boys. Swiping right on them. We have Neil and we have Drew. Hello. Hello. Thank you guys. Feel good? Yes, all is well. So first off, uh, I've known Drew for 15 years at least, something like that.

DREW:

Yep.

Anna:

We don't wanna age us off too much, so maybe we'll say like five years

DREW:

done.

Anna:

I have met Neil for the whole amount of four minutes maybe, and Drew and Neil do not know each other,

DREW:

correct.

Anna:

We're prepared to against tonight because to my knowledge, drew, well, drew I know is over 40 never married, correct. No children.

DREW:

Correct.

Anna:

We also know that Neil is over 40, never married, no children.

NEIL:

100%.

Anna:

You are both businessmen in the industry. Actors ad you have many, many, uh, accolades to your names, but we don't care about that on this show. We only care about love dating women, successes, failures, and whatnot. Oh, see, let's go. You're already making a sip. Go.

DREW:

Yep.

Anna:

So the first question we ask everybody is, why are you single? I'm going to Drew first.

DREW:

Just haven't found the right one yet.

Anna:

How long have you been single?

DREW:

Five years. Mm-hmm.

Anna:

And before your last girlfriend. What was the longest work before that?

DREW:

Four years. Four years. Three years.

Anna:

Oh, okay. So, so yeah. Squa, mono, serial, monogamist. Yep. Interesting. Neil, why are you single?

NEIL:

I enjoy. I love my peace. I love my freedom. And most important, I don't want to, I never wanna feel controlled.

Anna:

Got it. Okay. So you haven't found the right one. Mm-hmm. You enjoy your singlehood and you don't want to be controlled.

DREW:

Yes. Open. So, okay.

Anna:

Dating wise, uh, are you on any apps, drew?

DREW:

Yes, but I don't really, it's not like actively on them. Like I just look at it and go, eh, and then I'm, okay.

Anna:

So what apps are you on? Like in and Out?

DREW:

Bumble. Hinge and Tinder.

Anna:

Bumble. Hinge and Tinder. Okay. I'm about to say I have two more League and Raya currently,

DREW:

which you have to pay for, right?

Anna:

You don't have to pay for the league? No.

DREW:

Um, maybe the guys do.

Anna:

No, you can,

DREW:

you can

Anna:

pay to get more access. All of 'em.

DREW:

Yeah.

Anna:

But, uh, but you know what, it's, uh, I don't need more access 'cause uh, it's a lot of access already. Like I can barely different

DREW:

women as we discussed one time. Yeah. We, we can

Anna:

barely keep up. Yeah. Drew and I talked about this in a bar one time's. True. I opened my Tinder profile and I had 3,700. Like likes.

DREW:

Yep.

Anna:

And how many did you have Drew? I, there's

DREW:

like 20,

Anna:

so no stick. I'm, I look at yours,

DREW:

I'm like, are you serious right now? Yeah. I'm like, 3000. I'm like, she goes, what? Who do you have? Like hundreds. I'm like, no, 20.

Anna:

This is not looks thing. It's just men and women. Yeah, women get more swipes. But what I do think is that men just swipe, just swipe, swipe, swipe with no intention on potentially ever talking to you or dating you.

DREW:

I think it's more of a numbers game for guys. That's what we've been raised. Basically you just throw out a net and whatever you catch, you know, you take. So it's like, try a thousand if you get 10 back, there you go. Do you

Anna:

agree with that, Neil?

NEIL:

Yeah. You gotta remember it's, uh, 10 girls per man easily. So, so the numbers are always right away. This is not gonna move it along. And same thing, whatever you can catch.

Anna:

Okay, so wait 10 to guy, where do you get, is there a stat you mean?

NEIL:

Yeah, I believe there's like a world stat, there's more women than men.

Anna:

Can we look that up? Ratios are like two to one or three to one. In some cases. As in single men versus single women. Yeah. Yeah. Okay. There are more single men.

NEIL:

Okay. Look, there was a time, uh, and, and it feels like yesterday, mid two thousands, 20 10, 20 12 uhhuh, you go to the hottest nightclubs or Vegas. Automatically more women than men automatically. And that was just one thing I guess you would just hear everywhere. Sure. Yeah. There's more, there's more men than women all the time and that's just like a world stat or something. But now I guess, uh, we made it aware maybe, maybe that's not true

DREW:

on purpose. They would like put more women in the bars, let people put more men in the bars and guys would come spend money,

Anna:

which we did a bunch of clubs downtown. We did. We're in denial basically. My point is the club is still hip been happening for us. And I agree. I still to this day, I feel like women get let in easier. Yep, yep. Risk through. Because to your point then guys are in the line, they see it, but women go in, they're like, oh, yep. So I do think that's a business strategy and they

DREW:

willing to spend money in bottle service.

NEIL:

Yeah. And let me bring up one more thing. If you are going to Vegas, to a pool party, I used to do that a lot before. Same thing. You want the nicer day bed and so on. When I would get to the club, talk to the host the way I, I used to party, it's just me and I would have like five girls, that's it.

DREW:

Oh, because girls want free drinks. Yes. You can actually see a single guy by the himself to like, they know what you're looking for. I'll

Anna:

tell you that. We do. I mean, I don't know. This has like been ingrained since, since I've faked Id in Formula Yugoslavia ordering wine at age 12. We like free drinks. Yeah.

DREW:

But, and we also been trained to, or trained to provide the drink. Exactly. It's like, oh, it's like a way to have a conversation with you or to engage with you. Right. Yeah. I like that. It's like, lemme buy you a drink.

Anna:

Yeah.

DREW:

And now you're like, you feel like you're in.

Anna:

Yeah.

DREW:

Well the

NEIL:

best way, and this is, this is what's worked for me in the club scene, Uhhuh. Like if you're out partying the club scene, you wanna meet girls, like girls after to date

Anna:

Uhhuh,

NEIL:

you better be nice and invite her friends as well. It's much easier you're in.

Anna:

That's true. Much better. So, okay, so back to the, what I define as the Peter Pan syndrome, right? If you do a little deep dive, like is it that simple? You just haven't found the right one?

DREW:

Well. For example, like I just went with a friend to buy a car, right? And it was expensive car. And she spent like a lot of money and every detail she was going over with a fine tooth comb, like she was like, what's the scratch right here? I want that fixed. Why is there a dent in the leather? I want that fixed. You know? And that's only like 90 grand, right? For that car, which is a lot of money.

Anna:

Only 90 grand. Yeah, that's a lot. But now think

DREW:

about if you're dating somebody, like what the investment is as far as how long you're with them, the time you're with them, whatever. But why are we so keen on settling with that? You know, like you're spending all your time, which is valuable, all your money, which is obviously you worked for, to then just settle with somebody, you know, it's like why not? Also then like go over a fine tooth comb with them and be like, Hey, I want somebody that makes me happy. That hits all the things that I want.

Anna:

Okay, well, hitting all the things is not happening because no one, it's perfect.

DREW:

You

Anna:

can, but like someone who's, so my list is. It's pretty simple. I've gone over it on this show multiple times, but it's like, okay, I need to be attracted to you, obviously. Yep. Like, but again, that's the first thing. But again, my attraction window is pretty wide. I don't have one. Oh, I

DREW:

know for sure. Yes.

Anna:

I like, yeah, exactly. Drew. Drew Sand knows for sure. There's a wide, there's a

DREW:

wide wide range. Wide page of

Anna:

what I'm attracted to.

DREW:

Yes.

Anna:

But I do think that there's. If you have a super narrow attraction field, like down to like inches and hair and everything, yeah. You're obviously gonna have a harder time.

DREW:

Uh,

Anna:

for me it's like, or

DREW:

maybe easier time now you know what you want and you only go for that person. Sure. You know, but then

Anna:

you have, but then, okay. But then you'd really have to put looks as the most important, right? Mm-hmm. Because the, also that person and also being, let's say, intellectual, if you're into that. Yep. Or into football or, and great. In bed and a great, uh, cook. If they're all deal breakers, you're not, you are looking at like an AI person.

DREW:

Yeah.

Anna:

How long is your list?

DREW:

I mean, not as a guy. Not really that long, long, drew just goes,

Anna:

perfect, perfect, perfect. No,

DREW:

exactly. And like,

Anna:

no, seriously,

DREW:

honestly, like people always say, they go like, I don't really have a type. I'm just more like, like my net is so wide. I'm like, you, you don't have a type either.

Anna:

Yeah.

DREW:

And it's just, but I think more, it's like after attraction, there's like, I. Usually something else where you're just like, eh, you know, like whether it be, okay, gimme

Anna:

an, I

DREW:

like religion, for example. Somebody's too like Catholic, like, or too Christian. I'm always like, Ugh. Because like, they're just like, I don't know. Like, it's like, oh, sorry, I can't do this on Sunday. Or I don't know. It's like, I'm like, really? Like I you're that into that. I, I don't know why. And I was raised Catholic. I was raised, uh, Christian, you know, Uhhuh. But like for now, I'm just like, if you're that into like religion or whatever, I like, I had a girlfriend tell me, she's like, I fear for you. And I'm like, what do you fear for me? And she's like,

Anna:

wow. She's

DREW:

like, I fear that like, once you die, you're going to hell. Like, you don't, you don't believe in God anymore.

Anna:

Oh. And

DREW:

I was just like, okay.

Anna:

That I understand. I think you're, I think you are a little surgical, I think knowing you drew like, you know, little traits here and there will be like a no for you. Yeah. Just that's me pulling it.'cause I know you, but uh, uh, I do not know Neil. So what, what are your, uh, yess and nos?

NEIL:

So, yeah, very similar to Drew. Uh, born and raised Catholic. Christian, same thing. Uh, I'm open-minded too, and I've gone out with other girls of other religions, Uhhuh. Um, uh, and uh, yeah, I've noticed, and I stay away from the Christian girls that go to church every Sunday because they seem to be the angriest ones. They seem that, I'm gonna pray for you. They seem to be the ones memorizing the Bible. Like everything that the Bible says that you're not supposed to do, they're doing. Yeah. So it's all hypocritical. Like, look at what I memorized today, and I'm the number one person at the cla. I'm like, wait a minute. We're not supposed to be doing this kind of stuff. So they're, they're judging you. Okay. And uh, what I have noticed for me is dating women that are not Christian. Their actions are more Christian, yet they're not memorizing the Bible. They're not going to church on Sunday, but their actions are more Christian based as in conservative, staying home. Let the man lead. Uh, those kind of things. That's what I have ran into.

Anna:

Oh. Mega Christian. We are, we're taking away is, is, is has been challenging for both of you and that's like a no.

NEIL:

Yeah.

Anna:

Right. Religion is an interesting thing for me as well. Someone incredibly super religious of any religion. Yeah. I would have a hard time to adjust to that. Yep. And I have dated, never a Buddhist, but I have dated like Jewish Muslim, Christian, like I've, I've, you know, and again, there are different levels of those. Yeah. Uh, religions looks you pretty broad. Yep. Right. Finances? No, no, no. Good. Okay. We were out like drinking one night or you told me about some night where you were with some, some girl wanted to come home and have sex with you and you are at now it's your 40 plus. You're like, oh, I don't even wanna make coffee the next day. I can't be bothered.

DREW:

Well, no, it's more like she was too clingy, I guess. And I could tell that was like, like how am I gonna get her outta my house situation? So she

Anna:

was your type but too clingy

DREW:

right away. Exactly. Oh, like always just like, like too, like I just met you and she was too already involved. Okay. And was like, yeah, like I could tell, like it was gonna be like, oh I'm gonna come back to your place.'cause like I just crashed there. And then I'd be like, okay, well I got things to do. It's noon. Can you maybe? But you know what's coming. Exactly.

Anna:

Okay.

DREW:

Yeah.

Anna:

What are you putting on the apps that you're looking for? Long term? Short term. Long term. I don't know yet. Term. Long term. Term?

DREW:

Yeah.

Anna:

Okay. Over to you Neil. But

DREW:

sorry. Yeah, I was saying though like in that situation was also that girl wasn't a girl who I wasn't gonna see myself going any further than just sex with.

Anna:

Right. She wasn't your you, you felt it wasn't your jam. Exactly.

DREW:

I don't like if it was somebody I was interested in, then I was like, I like stay the whole day, stay the week. I don't care.

Anna:

But 30-year-old Drew might say, fuck it.

DREW:

Oh hell yeah. Let go. So

Anna:

that's what we're saying. I can sacrifice 1-year-old Drew is like been there up. Okay. What about your type I like.

NEIL:

Simple. Just a, a girl obviously takes care of herself. Mm-hmm. I like girls that are more tall,

Anna:

short, black, white, Asian, uh, fit

NEIL:

petite. I mostly go out with Asian women. Okay. I travel a lot to Asia, so most of the women I, I meet are Asian Uhhuh, uh, based, um, but a little bit minded to everything. Okay. It just never happens. You're

Anna:

drawn to Asian women. Yes. Yes.

NEIL:

It just, just never happened though, with other women, other demographics just, I don't know, just doesn't happen. Sure. Um, and so, and I like the women that are just very, I would say, yeah. More traditional, uh, meaning

Anna:

as like a man needs. And she cooks her cleans a little bit. Yes. Like as a traditional household. Yeah,

NEIL:

yeah. Traditional. Oh. Um, I really like a woman that, uh, that's not gonna challenge me. Instead more, she's gonna be there as a, as a cheerleader supporting me. So let's say if I'm going to work or audition, whatever that may be, she's, they're like, oh, how'd it go? You know, you're the best. I wanna see you do Well, uh, not, uh, challenging me or, or saying, well, today at the office I had to deal with this so you don't understand my life and so on. So,

Anna:

but can she talk about her life? Of course. And be like, Hey, this what happened with me today.

NEIL:

Absolutely. Yeah. When

Anna:

you say challenge you, what do you mean? Like, gimme an example of like a challenge.

NEIL:

I've gone out with very beautiful career-driven women. Uh, I've, for some reason I need a lot of doctors and, and they still want the tradition at home. Oh, so it, it's interesting where, uh, they're bringing up, uh, you know, their day at work and the drama with dealing with corporate and pharmaceutical and that kind of stuff. I've heard stories like this or clients and, uh, there I am talking about my day. But again, for myself, really, I, I don't, I don't really need to share too much about my day because what I do bring home, it's gonna be a completely clean slate. Free, no outside, nothing in the outside's coming into the home.

Anna:

Oh, you don't wanna talk about your day so much? No. No. So if she wants to talk a lot about her day, that's too much for you. I'm okay with that.

NEIL:

She, uh, I, I'm there to listen. If she wants it, advice, I'll give it to her Uhhuh, but I'm not gonna be there as an everyday person. This is what happened today at the office then. No, that's where it's like, no, that's too much now.

Anna:

Oh, I know that. Women. We do like to come home in general and talk about our day. Like again, like women can come after me, but I generally feel that's the case. I do try to call girlfriends and talk about my day more, but we'll start times with my ex and ex-husband that I try to do it and yeah. And every time I ask them, how's your day? Good, good.

NEIL:

Fine. Yeah, no,

Anna:

all is well, right, so, so I'm sorry. Like that part is like, that's just women, you know? Yeah. So if that part is you, yeah, you might have an issue. I mean, I don't know. Okay. What else? Does she have to know how to cook? Drew?

DREW:

No, no, no. She doesn't cook, doesn't cook. And most likely I, old school, I usually like to clean because I like it to be clean. You

Anna:

like it to be clean? Yeah, clean. I'm usually

DREW:

clean. Yeah. I like to do my own cleaning. I do. But you don't need a

Anna:

woman that can cook. No. No. How Fashion, okay. Uh, yeah.

DREW:

I like cooking too.

Anna:

No, me too. I like to cook, but you know, a lot of women find pressure in like these more traditional, if it's sold that way. Okay. What about. Do you want kids True still or, yeah. Sorry. Do you want kids? You want kids

NEIL:

open-minded to it, but that's a very serious thing. Kids

Anna:

are not on your mind. No. But would you date someone that has kids?

NEIL:

Yeah. Yeah. Okay. With that? Yeah.

Anna:

We're okay with that? Yeah. Because also in 40 plus that becomes exactly in,

NEIL:

she, if even meet a woman with no kids, you're like, what happens? Yeah.

DREW:

Yeah. Right. I will say it's a little, it's a little bit not like I turn off a little bit like hesitation when they say like, I have like, like small kids full time.'cause then it's like, well then like how, like, I don't know. Like how the, like free time kids. Yeah. I can

Anna:

tell you dating someone with small kids a lot harder. Yeah. Oh yeah. Small kids. It's, it's, it's like the hardest time when they're, uh, listen. Bigger kids, bigger problem.

DREW:

Exactly. Small children. You can like make that time consuming and

Anna:

draining. Uh, when I date, 'cause I swipe on a lot of dads. Right. Um, I prefer if the children are older. Yeah.' Anna: cause that's a little more chill. Yep. And to your point, the custody is a big thing. Yeah. Like full time. Obviously. You then, uh, drew are like, how's this gonna work? Are you, would you be okay with full-time, Neil? I'm okay. I actually, I've got like the kid moves into your house with the mom kind of thing.

NEIL:

Yeah, yeah, yeah. You know, it's funny. I'll tell you the, some of the women that I've dated have like a. 5-year-old he is, had a toddler, 6-year-old, and I'll, I'll tell 'em, come to my house, come to the beach, hang out. You know, a few girls want, I mean, bring, bring the kids. Well, you kids have no

Anna:

problem with kids.

NEIL:

No, I have no problem with the kids because what I've noticed going out with those mothers is that, hey, if I'm inviting them with the kids hang out during, they take a walk, beach, whatever that is, the park, the end of the day, the kid's tired, the mom's all, well go ahead and go to sleep in the other room and the mom wants to hang out, you know, do some watery stuff. Yeah. So if you can handle that with a single mom, she, she, she's, she'll wanna stay the night at the house. She

Anna:

wants to stay the night. Yeah. Because she wants to be taken care of.

NEIL:

Yeah. Makes sense,

Anna:

huh?

NEIL:

Yeah.

Anna:

Okay. So you find that single moms might be, it's more easy to get laid with single moms.

NEIL:

That's automatic. Much easier. Yeah, it is much easier. Yeah. Yeah,

Anna:

that's what I'm, okay.

NEIL:

Automatic. Seriously. From a guy's point of view, Uhhuh, if a guy meets a single mom, he's, oh, that's the first night automatic. Really? That's how most guys are gonna be thinking.

Anna:

Really?

NEIL:

Yeah. Most guys interest.

Anna:

Have you been with any single mom? Because the guys, I

NEIL:

mean, I'm like, you know what, I'm sorry. Before I forget here. If you're hanging out with your buddies, Uhhuh, and the guy says, going out with a single mom, and if the guy says nothing happened on the first night, they're like, dude, you're like, what a waste. Like how could you, you're a failure.

Anna:

Really. What if he likes the single mom and wants to like wait a little bit to have sex? Maybe he's like really into her

NEIL:

that I, you know what's funny is I've met guys like that and the single moms kind of get upset'cause they, they're like single moms already, from what I've seen is more, Hey, you know, I already have a child and let's go have a good time.

Anna:

Ah, I mean, I'm a single mom. I'll be honest. If I like somebody. I'm not having sex with you the first night,

DREW:

but you see what, but that's what I'm saying, like, women are the ones that put this like, like, like timeframe and restrictions on things.

Anna:

Okay. So if I have sex with you the first night we meet, we on a first day we match online, we, we go on a, we have a couple of drinks or whatever we wanna do. I go home with you at night and we have sex. Does that rule me out as a long time girlfriend?

NEIL:

No. No. No, no, no. I'm gonna tell you right now, quick story. Why

Anna:

do we do these games?

NEIL:

Yeah, exactly. Why do we do these games? Exactly. No. You know what's funny, Justin? No, I, I met some women on the first night and had some pretty good, pretty long relationships.'cause they just like a solid year and then after that you're just like, Hey, is this gonna progress now? So it had nothing

Anna:

to do with it. No. The one said had nothing to do with it. I

DREW:

remember we talked about this too, I go, um, and you're like, that's not true. Where it's like, if you're not making out with the person the first date. Yeah. It'll never happen. Hundred. And you said I tea. Yeah.

Anna:

No, I actually do make out on the first date. Yes. Yes. That I do. And if I don't, I always go like, thank you. I had a nice time. Yeah. And I tried to keep it to like, I mean, I've been out, one guy I was with for, for like two hours and I knew like maybe he wasn't bad. Like he came in and sat down. I was like, okay, you know, bad in real life. And then we talked, it was like 40 minutes in. He's like, yeah. One time I picked up this 24-year-old on a plane. And, uh, I mean we were together for like two years and, and as he started talking,

DREW:

how old was he? He was how old? He was 50. Okay. 50. And she was 24.

Anna:

Yeah. That story alone gave me the ick.

DREW:

Yeah.

Anna:

And after that I was like, this was a nice night. Thank you so much.

NEIL:

Well, first of all, no guy in a day should ever be talking about ex and other dating. Like that's just a you good one. You should never do that.

Anna:

I actually

NEIL:

agree. And I, and I've been, I've gone out with girls that try to trick me to that. So tell me about your ex.

Anna:

Oh, that's Dec I don't know what, I've got the question like, Hey, how, like why are you basically, why are you single? Which is why we start with this. Yeah. Like, why are you single? Like, what's your deal? And I'd be like, Hey, my relationship ended over summer and we were together for six years. That's, I'll go, I'll go there. Yeah. Because I think it says something about me like that I like long-term relationships and you know what I mean? But I agree with you. Apart from that, no.

DREW:

I guess it's good to be honest, but also it's like sometimes you don't want to necessarily.

Anna:

Overshare

DREW:

your whole house on the first date. Yeah. S flood lightning apparently. Yeah. Yeah. Flight lighting

Anna:

is when you're like, blast with your stuff first.

DREW:

And if you like it, then you like it. If you don't, you don't.

Anna:

Yeah. I mean, this is interesting. Okay, so Neil, are you on, um, are you on the apps?

NEIL:

Well, here's the funny thing. I had, I, I have, I've not been on any dating apps for quite a few years. Uhhuh, I completely have just quit it. Oh. And I have done, and all the girls that I meet are gonna be outside

Anna:

in the wild.

NEIL:

In the wild. I are. Yeah. Yeah. And nothing, not a bar, not like a social place. It's gonna be your. Just Hope Foods someplace normal place. And where,

Anna:

what is it normal? Terry Jones, the bus stop. Like where's a normal place bus stop.

NEIL:

Yeah, that could be, uh, like at, uh, the, give

Anna:

an example,

NEIL:

sushi restaurant. Okay. Where do you meet

Anna:

your last fling? Where did you meet her?

NEIL:

Actually at a, uh, ramen. Like a restaurant?

Anna:

In a restaurant?

NEIL:

Yeah. Okay. Like one of the servers? Yeah, like one of the girls, like barely could speak English, that kind of thing. And just there and Hey, how are you? Oh, okay. And, and things like that. Yeah. Yeah. You're

Anna:

just picking up the interest. I love that. Yeah. I have tried my fair share of flirting with bartenders with which one time, uh, drew and I went out. And I did like the bartender

DREW:

hit on him hardcore and I did

Anna:

hit on him hardcore for like 20 minutes I think,

DREW:

and then he go and then, and he goes, well, he's more my type. Oh man.

Anna:

It's true. It's, wow. I was, I felt flat. He was the bar, the bartender was bating for the other team. Yeah, the disappointment filled the room at that point, you were

DREW:

so into him too. You were like, I was so into him. He was so hot. His hair is so good. I love his hair. Hindsight makes sense why his hair was so good. Yes.

Anna:

Now he makes sense. See, it's

DREW:

also so easy if like, she'd be like, I went out and met out a guy last night and like guys are like, I got nothing again.

NEIL:

Yes. That's another thing I forgot to say is social media. If you're active and, and keeping it real, like posting your real stories or whatever that is, you'll start having people, Hey, how you doing? Or, I like this, and so on. That's another way. Oh. I'm just always active on my social media. What media Active better.

DREW:

Do think, how do women

NEIL:

know that you're media? On social media? It, it's everything. It could be from single older mothers, women in their fifties, women that are in their twenties and thirties. It, it ranges. So

Anna:

they're following you?

NEIL:

Yes. Huh. That following or I've gotten likes and messages, yes.

Anna:

Okay. Social media. Uh, I don't really pick up on social media. I literally just use the apps and the wild and it's plenty, but I think if you're not on the apps, I understand social media. Yeah. That makes sense. I mean, we're just trying to connect with people. Yeah. You know. Okay. Give me each of you a terrible first aid story. What is your, one of your worst, one of your worst first dates? You already my

DREW:

story.

Anna:

Well go for it.

DREW:

Uh, back when I was on social media or on dating apps, Uhhuh, I was in Charlotte on Tinder and met this, I mean, she was really attractive and obviously like. The photos can be deceiving. So when she showed up, she actually looked like her photo. And I was like, wow, this is refreshing. Uh, went to a fancy restaurant and it was great. I mean, we got along perfectly. We had drinks, everything else, and we went to another bar. We played pool. She's got good at pool. I love playing pool. So that was fun. And then it's like, well, let's go back to the hotel that I'm staying at. We'll leave your car there. We'll get a drink and we'll go somewhere else. And she's like, let's go. So we get back to the crew hotel, which again, it's the hotel I'm staying at. All the crew members are there. We frequent the bar a lot. So the bartender knows me, the manager knows me, and we get there and all of a sudden, like a light switch just flips. And she was like, why are you being so mean to my friends? And I'm like, uh, who, what? Who are your friends? And she's like, you're so condescending to them. Like, what do they do to you? And I was like, I. I'm sorry, like did I miss something? Like who were your friends that I was condescending to? And then out of nowhere she just starts yelling at me, like being like, you're an asshole. I can't believe you're that way to my friends. Like, I can't believe you do this to me. And I was like, what are you referring to? And creates a scene. And of course I have coworkers that are there at the bar as well, and they're like, what the hell is happening?

Anna:

What is Drew doing?

DREW:

Exactly. Yeah. So then she's like, I'm leaving. And I'm like, yeah, you should leave because I have no idea what's happening, right? But then I was like, oh God, no, she's gonna drive. We've been drinking a lot. She can't drive. So I trace after her, I'm like, can you please just not drive right now? Lemme get your keys. You can crash in my room. Like I'll sleep on the the couch. You sleep in the bed like, but I don't want you driving. And she's like, well fine. Even though you're such an asshole, I'll go back upstairs with you. And I was like, whatever. So that

Anna:

nice of you to make sure she's not driving. Yeah. You didn't have the responsibility. Yeah. Well, you as a human you did, but not all guys would. Mm-hmm.

DREW:

So get up to my hotel room and then we get into the room. Yeah. She goes even more ballistic and was like, why are my dogs missing? Who let my dogs out?

Anna:

See, Drew's a good guy. Yes. You should find somebody. Okay, go ahead. So I let her in. Mm-hmm. So

DREW:

my house keys were on the counter. Um, she takes my house keys and then like makes 'em into like, you know, a fist and then tries to stab me with my house keys.

Anna:

I'm sorry, I'm laughing. It was obviously

DREW:

not fun at the time. Well, obviously I was like, what is happening? You know, and like, so I, oh my God, drew, I'm just like, you need to calm down. And she's like yelling and screaming, trying to stab you with my keys. And I literally had to like, put her in the bed and like tuck her in so she couldn't get out. And then like, she finally just passes out on the bed and I was like, Jesus Christ. And so I passed out on the couch and in the morning he wakes me up and she's like, hi, did I get weird last night? And I'm like, uh, yes, you can say that. And she's like, I'm sorry. I got, like, when I was younger I got hit by a car and unfortunately I had a little bit of brain damage. And when I drink. I can get crazy and I'm like, could you maybe have told me this beforehand? You maybe could not have drank

Anna:

on the dates. Oh my God. This is a crazy story. I mean, it's hard to top that. It's a blind date.

NEIL:

Yeah.

Anna:

Neil, any first date stories that stands out for you? Yeah,

NEIL:

yeah. So very interesting. Kind of similar. Um, so I had a first aid, uh, I travel a lot to Asia. Mm-hmm. So, uh, I met a girl that's in Japan. Mm-hmm. Uh, talking through the media and then I was like, okay, well I'm visiting Japan this time of year and said, come on down here. You stay at my house, stay with me. So, fantastic.

Anna:

Hold on a second. You stay, you did not know that she was a stranger.

NEIL:

Yeah. Just know through, through online media talking. That's it. Right. And you're

Anna:

not scared to stay with a stranger? No, no. Different

NEIL:

guys. Yeah, different guys. Pretty girl. And we did face chatting and all that stuff. Okay, fair enough. A few months already. Okay. Nice. And anyways, uh, so I arrive, picks me up from the airport. We spend the whole day. I arrive at five in the morning. So we spend the whole day. City drinking, having a good time, just having a blast. Mm-hmm. Finally, the night's over, get back to her house. Uh, then after, you know, everything's well, stay the night, sleep with her, the whole thing. Uh, then next thing you know, at 7:00 AM she wakes up. Uh, mind you, this is March, uh, in March in Japan. It's snowing. It's very cold. Uhhuh after wake, wakes up at seven and then, um, taking a shower. She switches the button to. The water to be cold water. It's freezing. It's freezing. Yeah.'cause you have to push a button to turn the hot water. Oh, so you

Anna:

are taking the shower and she pushes a button. Yeah. Yes. That then switches it to cold. To

NEIL:

cold.

Anna:

Yeah. While you're in there in the

NEIL:

shower. It's freezing. Does that I said, Hey, let me just finish first. Let me just finish really quick. And then after I put my towel on the, she, okay, you need to leave now. I'm all, I didn't book a hotel. I don't know like where I can go right now. No one's gonna answer the phone if I call somebody, like where do I go? And we're staying outside of the city, Uhhuh. So it's a good train ride and the whole thing. And I, I know my way around, but this was a whole new area. A little different kind of more countryside. Sure. So anyway, at seven in the morning, uh, I'm ready. Just putting on, you know, my, I, luckily I took a quick shower and I'm carrying my suitcase in the snow. I go to the train station. Station's not open yet, and she already just kicked me out. Oh. And then I'm like, what do I do? You know? I'm like, I, I can't get ahold of nobody. This, this is like, the timing's really bad right now. Uh, so she'll just go to the train station and then you need to leave. Now. How, what

Anna:

triggered do you think

NEIL:

that, I don't know.

Anna:

So you, this is Acra, so it's almost, it's after

DREW:

sex, which is also weird. Yeah.

Anna:

It's, it's, uh, yeah. That is, uh. A one night stand that's not even, it's a, what would we even call that? And she was single.

NEIL:

She had night her own place, everything. Yeah. Oh my God. So it wasn't like a husband or nothing like thinking, are you? No, no nothing. Totally single. Very friendly. The whole thing kicked me out after then, you know, finally the train comes, I take the train like

Anna:

a one night eviction. Really? Yeah. Yeah.

NEIL:

Yeah. That was wild. Because

Anna:

jet,

NEIL:

jet lagged too. Yeah. So you're waking up, you're like, whoa, the time difference, everything, you're just, it feels like you're drunk and well you kind of hung over. But yeah, luckily after that caught the train, hung out at the station. It was freezing cold in my Does your

DREW:

home?

Anna:

Yeah. Okay. So I was general hot tip. I think's like, do not plan No. On your one night stand to Zerbe a hotel. Yes, yes. Is the takeaway you Yeah. Still get, yeah. Obviously it was hoping to be a week flip. Yeah. Yeah. No, no. I stay for about a week, you know. So, no, stay here, let's hang out. And that was it. It's still a stranger. Yeah, like FaceTime or whatever. So I think that like stranger danger kind of applies, right? So, but I also think that like what we learned from Orna and Matthew Walters who are like relationship experts, that they were like when we meet somebody and we talk a little bit FaceTime, texting maybe even a day or two or three, our mind will fill in positive blanks about this person and where this can go. Yeah. Which is male and female trait. Yeah. So we will naturally just put someone in a positive light and therefore make decisions based on that, which could sometimes be a little Sure. I mean I went on a first date to someone's house that I had never met and I think we had only texted all my friends. Were like, are you crazy? You know, I survived and it was all fine. However, I understand now how cool good it is. Yeah. So I've not been on all these dates, so we have to be careful out there. Okay. Speaking of being not careful can come with a lot of regrets. We have a lot of game that we call regret roulette. Okay. You are gonna spin each spin this wheel. It has a bunch of categories on it.

DREW:

Basically I spin it. If I say land on worst sex, I tell my worst sex story.

Anna:

Yes sir. Okay. Yeah. Of regrets around it. I know Drew has many regrets. Worst text.

DREW:

There you go. Worst

Anna:

I feel it's worst text.

DREW:

That's a hard one.

Anna:

There's so many bad texts.

DREW:

Yeah. As far as regret goes, I guess I could say that I have broken up with somebody over text and I regretted it.

Anna:

That is the worst text.

DREW:

Yes. You broke up with someone on text? Yeah, we were only dating for like three months.

Anna:

Only dating for three months and you broke up via text.

DREW:

Like she was not available. Are you fucking kidding me? She was not available. I couldn't have call her like we were. I was on another show. I was, she wasn't

Anna:

available. Was she on the moon? No.

DREW:

Basically, I was on another show in New York. She was on a show in, I don't know, somewhere like in like Australia or something,

Anna:

Uhhuh.

DREW:

And every single time I tried to call her, she was not available. Like it was also a, it was a bad relationship to begin with. Like anytime I would try to talk to her, it was always like, I don't have time for you. Like I'm too busy, blah, blah, blah, whatever. And I was Would this

Anna:

be her version as well?

DREW:

I think so, because like the text was like, I'm like, Hey, I don't think this is working out. Like are you just not available for me? Whatever. And she goes, I get it. Cool. Thanks. And I will say like. When I ran into her again like a year later, Uhhuh, she was not that cool about it. And she's like, oh, there's asshole. I broke up me over text and I was like, oh, like I didn't know what to, you know, like you weren't there. Like I, oh my gosh. I don't know what to say. Like,

Anna:

I don't know. Okay. Yeah, like,

DREW:

I, I was rather than a voicemail. Did you have

Anna:

to do it that second? Was there another shake? I, I actually don't know. I will say one of these things, I don't dunno, because a voicemail, you fucking called and you just went to voicemail. That's different. I will say the reason behind

DREW:

it though was also because I was falling for somebody else in New York and I didn't want to That's

Anna:

what I'm saying. You are a rush. Exactly.

DREW:

I was like, I feel worse. Cheating.

Anna:

Okay, that's good. Amanda doesn't cheat. I like it. I got this lady writer in the wings and 3, 2, 1 breakout. I'm good. Therefore I don't cheat. I just broke someone's heartbeat. A text, but, okay. Worst text. That is the, the worst text.

DREW:

But also I was 20, well, how old were you there? 27, 28. We, we were fine. And again, like I got

Anna:

Okay, fine.

DREW:

And again, it was, you're better

Anna:

now. You would not have dump on text now. Course I, no. Right, no. Fine. Stupid decision I think, honestly. Yeah,

DREW:

that's what we said. Regrets. Worse. Text. I one

Anna:

time got dumped at LAX on the phone by my boyfriend who was supposed to pick me up and Oh man. Stood there with presents and had presents for him and I was like schlepping my luggage and I was like, Hey boo, where are you? He is like. Yeah, about that. I up, I was like, oh man, fucking asshole. Alright, Neil, go ahead. Spin the wheel. Ghosting.

DREW:

Um, picking up ghosting

Anna:

a regret regarding ghosting. Did you ghost some near really badly knows. Did you break any hard? What's,

NEIL:

you know what's, I'm a really nice guy. I don't ghost anybody, but I've been ghosted a bunch of times, that's for sure. But really, I, I don't, you never ghosted anybody? No, no. I'm always nice. I, I'll send a message and,

Anna:

and be like, Hey, it is not working out. That's the

NEIL:

point of ghosting. Yeah. What is, yeah, I, I don't, I think that, I, I wanna say respectfully, I think that's a woman thing though. Ghost more than guys. Oh, Neil, you stepped on the towel. I've had women ghost me. Like, I mean, like, like crazy. You know

DREW:

what,

NEIL:

you know what? I'm sorry. I did Ghost a girl. You just brought something. It just, just popped in my head. I did ghost a girl. Let me, let me tell you this right now, okay? Text a girl a few times. Hey, you wanna go out on Friday? Yeah, we're going on Friday. Okay, when do you, you know, where do you wanna meet? Whatever. I didn't hear back till Friday morning. This was, and, and I was just like, you know what? This girl's like, every time I've text this girl, I've known her for about a month. It takes a week to respond

Anna:

Uhhuh.

NEIL:

So after on Friday when she said, okay, we can meet at this place. This is Friday morning, after, from Monday, confirming, I never respond.

Anna:

Oh

NEIL:

yeah. I just automatically, my head, I'm like, you know, fuck this. Yeah. I didn't respond. I, so yes, I did go with somebody. I just, I just remembered that.

Anna:

I mean, that's fair. Okay. You gentlemen are obviously the kings of, I think, spotting red flags.

DREW:

I love red flags.

Anna:

So we are gonna give you guys two little props. I'm gonna read a bunch of statements and you're just gonna say if it's a red or green, green flag, here are your flags. Yeah. Drew, here's your flags, Neil. It's just solid.

NEIL:

Okay.

Anna:

Okay, here we go. Uh, four. Four. But just like you, she has no kids and has never been married. Green flag, green flag for both. Okay. Which would be good. I drew have a question. Do you feel that you get less swiped on. Because you have no kids and never marriage green flag.

DREW:

Yes.

Anna:

You think that happens? Yes. Yeah. Yes. What about you?

DREW:

I mean, I, I guess maybe. Sure. I don't know. Girl comes up until like the second of their date. The past. I, I think women love dads. I

NEIL:

think women love men that are fathers.

Anna:

Yeah.

NEIL:

Think so. See that Dad, I'm tell you, or man, I'm a little

Anna:

discriminated. I do swap an occasional, not never marry no kids, but I'm a little scared You have

DREW:

kids.

Anna:

Yeah, but can I tell you, can I tell you what? It's for me. I think that when I see a man in their forties or fifties that never, no kid never married. I fear that since I want a relationship, this man is terrified of commitment.

DREW:

Why did, yeah,

Anna:

so then I don't wanna waste my time.

NEIL:

All my buddies that are my age, we grew up together and they're all now dads and they got the dad bod uhhuh, man, these guys need, they got girls throwing themselves at 'em.

Anna:

But do you think there's anything to that that you guys can't settle down? I said, I'm just with fear. So do you think your standard is too high? That's my point. I swear

NEIL:

nothing to do with standards. I love my freedom. I'd love to meet a girl who says, go do whatever you want. Come home later at this time and not try control. No, that's normal. I would love that. I would love that. But I do believe in this time we're in now, a lot of women are a little more demanding or try to control me or, or have certain demands, and I'm just like, no.

Anna:

I feel like there could be a whole Neil episode that we may not have time for it. I a lot of crazy stories. Yeah. Okay, let's go for it. Uh, another one. A girl who dated one of your friends previously.

NEIL:

Red flag. Red flag. Oh, just stay away. Wouldn't do that. Yep. Just, just No, it's just a bad idea. Yeah.

Anna:

Oh,

NEIL:

wow. I did that like high school. Not fun. It's just a bad idea. It's not good. I've had my friends ex-girlfriends hit on me after. I'm just like, no, I'm not gonna do it. No, don't cross that line. Don't, it's just, even if you're not friends with that person or anything later or just in that circle. No. It just creates problems and it's just like no awkward. Exactly. It's, yeah. No,

Anna:

the kind of person. Who does not like to be alone, and they always have a packed social schedule.

NEIL:

Green flag? Green. Green. Yeah, green flag. But I'm gonna give you the reason why that's a green flag. Mm-hmm. Any guy normally is not gonna be waiting at home for her. He'll say, sure, honey, go do whatever you want. He's gonna do what he wants. And then when she says, can I come see you? Oh yeah. Come on over then.

Anna:

Okay. We like busy girls.

DREW:

Yeah. Yeah. Okay. As long as there's time for you though, as well.

Anna:

Sure.

DREW:

Yeah. Yeah.

Anna:

Okay. If I'm gonna ask you this, a homebody girl. Yes. Green flag. I love homebody girls. Oh, I love homebody

NEIL:

girls. So basically anything right now we're, we're promising that we're all, lemme tell you, you go out with a girl that's a homebody, you're saving a lot of money. She's happy to come over, watch movies on Tuby or something for free. She even like will make food sometimes. I've had plenty of amazing women like that. Yes, I hear you.

Anna:

Okay. A woman who still talks to a bunch of her exes.

NEIL:

Green flag. Green flag. But green flag. Let me tell you why. Because the guy's not gonna be waiting around. Same thing when she's all over the place. When she has time, she'll come looking for you and guy's, all right, the door's open. Why not to the

Anna:

ex a lot. That's okay.

NEIL:

I don't, I don't mind. But here's the thing. I'm not gonna be waiting around for her and taking her serious.

Anna:

Oh, they talk out to the exes. That puts them in a certain category. Yes. Yes.

NEIL:

I think also you'll still sleep with 'em. Yeah. Why

DREW:

not?

Anna:

Of course. No, I get it.

DREW:

But like, I guess it would be like, what is the relationship. Like, you know, like is it like their best friend or is it like more flirty? Like are they I don't like,

Anna:

no, I hear you some

DREW:

caveats. I hear you. I say, green flag doesn't bother me. Yeah,

Anna:

there's a, there's basically a barometer on the excess.'cause I agree. Someone who talks to the excess all the time, I don't enjoy that. I think that's not normal. But someone who's friendly with the ex and a occasion check in, that's fine. Yeah. Uh, woman who says she's. Ethically non-monogamous. But she wants a relationship. She wants to be in a relationship with you, but she wants an open relationship. Yeah, A

NEIL:

green flag. Yeah. Red flag. No.

Anna:

Lemme tell you why it's green. Hold on. I gotta be

DREW:

seen. I gotta only date you, but you

NEIL:

Everybody else. Yeah. Red, red

Anna:

flag for Drew. Green flag. Green

NEIL:

flag. Because same thing. Okay honey, go do whatever you want. You call me whenever you wanna have a good time and that's it. But in a relationship. But except with you. Yeah. Are you

Anna:

okay in a relationship

NEIL:

to have someone She's gonna be thinking it's a relationship.

Anna:

Oh,

NEIL:

but so you are out there

DREW:

cheating as well? Well, yeah. That what happens. It's open. Open for both then. Yes. But it can't be like, well that's not gonna work. Cake. Both.

NEIL:

It's not gonna work. Open vote. But any guy is just most normal guy is just gonna be like, oh yeah honey, we're monogamous. And of course you do whatever you want. No, he's guy.

Anna:

Okay. Oh, okay. So ethical non-monogamy is a deal breaker for Drew. Yeah, it is not for Neil. Basically, if you were in a relationship, Neil with someone committed, right? Like what was your longest relationship?

NEIL:

Yeah, that was a while. Like 3, 3, 4 years. But it's, I been a long time. It last four years. Yeah. Would you have been

Anna:

okay if she said, Hey, I want an open relationship? No, absolutely not. Exactly. Absolutely. That would

NEIL:

be a red flag. Okay. Yeah. Okay. Yeah.

Anna:

Alright. A Disney adult

NEIL:

Red flag.

Anna:

Red flag.

NEIL:

The, the kind that like

Anna:

go to Disney. Disney, they go a hundred times a year. Wackos

DREW:

just like red flag be. Might as well be Christianity. Yeah. Okay. Like

NEIL:

what is the deal? I mean, yeah. We see some women's, a cult. If you mean, if you see a woman on her profile picture with the Disney ears or whatever, it's like, oh, forget just run lights or the Star Wars. Just like,

DREW:

no,

Anna:

it's problems. Okay. Any franchise and not good. Okay. Go ahead.

DREW:

I don't mind going to Disneyland. It'll be fine, but like Exactly. They're like, I, I go once a week. Yeah, yeah. No, they're just, they're just whacked out.

Anna:

I think it's fascinating. How about that? Um, a woman who poses with her cats in all her photos on the dating gala. Red flag. Red flag Flag Away from

NEIL:

Cat. Women.

Anna:

Okay. No cat.

DREW:

Women not against cats. It's just like you said, they're like, every picture is them and, okay. Would it be

Anna:

different? There was a dog in every picture. No,

DREW:

it's okay. I'm

NEIL:

a dog person.

Anna:

Oh,

NEIL:

but also, oh, you be

Anna:

okay with dogs too? Yeah. Why are we just against cats? I met women that are dog women that are dog lovers are,

NEIL:

are so like super friendly and nice.

Anna:

Oh, ate. So you both give a red flag for a woman who poses with all of her cats or a cat. But if a woman has a lot of every photo with a dog, it's a green flag

DREW:

again. Dog person. Dog person. Let me give you one. Get

NEIL:

along with a conversation. Let me work for the cops. Yeah. Let, let me give you a story. If you meet a girl online and her profile pictures, like hugging the dog or something, that's like a pretty good girl. Yeah. Okay. And like, okay. That's a nice one.

Anna:

I like dogs and cats, but you know,

DREW:

so a guy had all pictures of him hugging a cat. Would you be like,

Anna:

uh, I will tell you, hard, hard left. That was, that would not work. See, so, uh, thank you for playing. Uh, red flag, green flag. Good game. Oh, that's fun. We learned a lot from you guys. Now again, drew, I think you are into a little crazy. Yeah, a lot. Crazy.

DREW:

Tend to go a lot crazy,

Anna:

right? That's maybe why it's not working out.

DREW:

Probably. It could be.

Anna:

I've dated a lot of growth. I don't even know their name. But, oh, you don't even know that's, but then you haven't dated them.

NEIL:

No, but there's girls that gone out with, when I say I don't even know their name.

Anna:

Oh, interesting. That happens a lot I think. What? What do you say? No, it does it like, I don't think so. I always know who I take Cole. I know their name. Yeah. What do you, so you go like, Hey, you meet them, they go, Hey, I'm Caroline. And after that you just say you, you call them you for the next day. Yeah,

NEIL:

exactly. It was pleasure meeting, meeting you. You know what, here you go. This is what happens honey, sweetheart. Where do you wanna go, honey? Nice to meet you honey. Hi sweetheart. That that's a thing.

Anna:

Anyone ever turn around and be like, what's my fucking name?

NEIL:

If that does happen, tell me what is your name?

Anna:

Oh,

NEIL:

don't even try to hide that. Don't, don't try to hide it. Agree.

Anna:

I agree. Don't

NEIL:

hide it. Just tell me. Yeah. Another one too, if you wanna, if you're testing a guy, ask him what did we eat for dinner the other day? Or what was our first meal?'cause most guys don't remember.

Anna:

I don't have the need to ask a guy if he's dating multiple women, because I know he does. I know like I have a roster. They have a roster. I'm also seeing multiple people,

DREW:

I guess like you said, like, like winning is like, you hope that you win. Versus everybody else. Like you're the winner, right? Like you're the one that I'm the wrong if

Anna:

I like him,

DREW:

that they don't wanna go after anybody else anymore. Correct. Yeah.

Anna:

And I'm hoping that also at 40 plus that dating group, we remember, uh, usually people remember a time even without the internet, we remember dial up. We definitely remember a time when there was no cell phones. Like there's a lot of the digital revolution that we remembered when it wasn't here. So I, I actually think that's an advantage to us in online dating because people are tired of swiping and Yeah. Like, yes, people always say, oh, there's an end endless supply. And they keep looking for the better thing. Yeah. To an extent. But we also wanna be like, just get off them. Right. You just wanna, oh, there is hope of meeting someone that you cherish and, and, and like Yeah, absolutely. And, and there's a future with, you know, so speaking of daunting bios, people put some crazy stuff out there on their bios to attract, right? We every week have something called biohazard.

DREW:

Okay.

Anna:

Where we pull sometimes funny or worse bios. Lemme know what you guys think. Here are two favorites. I

DREW:

do you, do you read bios? No. No, guys

Anna:

pretty much don't read

NEIL:

bios. Let's just get the pictures. All right.

Anna:

You don't even read the bios.

NEIL:

Bios. So

Anna:

if I put in my bio, like

NEIL:

you can literally put how

Anna:

smarter are

NEIL:

if you're on dating apps. Yeah. And this is what I did in the past. I have to put something. My bio was my Instagram profile page and that was it. Oh, you wanna get to know me? Get on my Instagram. You'll see there's

Anna:

some good bios though. Yeah. I'm gonna read you one anyway. You should be reading bios. Copy. Okay. Hey, this sounds like a woman, woman for definitely Drew. Let's go. I enjoy skinny skiing and going to bull fights on acid.

DREW:

Let's go. Let's see, let's move. I mean, I'm interested, I wanna see what this involves. She's

Anna:

interested in this fight. I'm bull fight. I mean, would you swipe on that woman? Yes. Yeah. Wow. On that one. No, I would skip. It's a lot. One, I'd skip. Okay. I am intrigued. Okay.

DREW:

I wanna see what a bull an acid is.

Anna:

See, this is why you're single all, here we go. My other favorite profile of the week, this girl, this, this girl who knows, who knows Neil, maybe she's for you. I'm very sick of pretending to be a cool, laid back girl. So people want to date me. I am literally balls to the wall. Insane. And that's okay. Pussy is immaculate. Head game is otherworldly. I will treat you right. And I will also cry every day. High risk, high reward.

NEIL:

No,

Anna:

I'll

NEIL:

send I if she's, if she's really high, she's on full of herself, send one message. Maybe she responds and says, let's go and have a good time. She doesn't. She doesn't.

DREW:

Okay. Okay. I would say no. I feel like she's already full of herself and Oh yeah. That's for sure. Yeah. Yeah.

NEIL:

No, absolutely.

Anna:

That's, I read this to, uh, a friend of mine, Gus, and he was like, sure, high risk, high reward.

NEIL:

Sure. Yeah. The way I'm thinking, Hey, short term, good time. That's it. And if it builds, it builds.

Anna:

Well remember like in the eighties when people were like, there was like VHS dating tapes. I'm looking for someone who's looking for me. I have two cats and I don't know how to ride a horse. And my goal in life is to have my own religion. I was a flop at canoeing. I'm looking for a romanticist. That's your camera. Neil, you ready? Yeah. And go ahead.

NEIL:

Hey, I'm Neil Bentley Fierro. I love hiking beach, uh, and Italian food. So if you want to come out and uh, just have a good time, let's go. That was so good. Dang. Okay.

Anna:

Drew's dating by, Hey, we wanna help all our dancer, including myself, find love. So let's go Drew.

DREW:

All right. All right. My name is Drew. I would call myself a hopeless romantic. I will treat you like a queen or a princess, wherever you want to be. Um, I love long walks on the beach. I love going on hikes, so my dog and with you, and also love Korean barbecue. And finally when we go back to whether your place, my place, I make excellent espresso martinis.

Anna:

That was great. Espresso martinis. I've correct. It's your place. I haven't got espresso martinis. Yes. You had, it's a lot to keep up with the profiles Instagram instead of jaw. Right. You have to be active on your phone finding, swiping. You have to go out a lot, which costs money and whatever. Right. So, but when you follow

DREW:

so much money these days,

Anna:

it does. Um, do you pay a lot Anna? Or

DREW:

Yeah. Yeah.

NEIL:

You, if you wanna hear one st. A a simple story. When I go, when I go on dates, I pay, I know, yeah,

Anna:

yeah. We pay when I go out. But here, exactly. How about now? So

NEIL:

expensive for you, Anna. Yeah, but how about this? Now the women get, some of the women I've dated get upset that I'm paying. They don't trust me that I'm paying

Anna:

what, what's wrong with these women?

DREW:

They don't trust me. Can you gimme their

Anna:

number? I need to talk. Think they're more

DREW:

hoping that you're not expecting something else from between. No, no. Not even that's No, no.

NEIL:

It's, it's a culture thing. It's a culture thing. Oh. Oh. So what happens is they'll be like, uh, oh, he paid for the whole thing. Like, uh, no, no. I could pay for my own. It's just not right. And they get upset, like, well, you know, it's the western country, you know, if I'm offering to pay for you,

Anna:

I have,

NEIL:

I I have to

Anna:

pay on the third date. That's nice. Okay. That's very nice. Third date. That's nice. I, I, because I kind of feel like, listen, we've done on two great days. Thank you so much. Yeah. I really wanna pay for today all that. It's like a, a gesture that I see you, I you, that's you. So that's what I've done. No, I'm gonna really shift, we split down the middle and everybody works and, you know what I mean? That's nice. That's a nice way to do it. Yeah. So I think I, it is just at, at the courtship, I feel like there's something about, you know, what's that first impression? First impression. Yeah.

DREW:

I mean, even my last relationship, like I would say honestly. 95% of the time I paid, I always drove.

Anna:

Oh

DREW:

yeah.

Anna:

That must be nice.

DREW:

Yeah, always did. I

Anna:

also paid for 95% of everything, and I will never do that again. And someone said to me, oh, you're I, oh, I went on a date with another guy who also did not make a lot of money. And I said that to him, I'm sorry, I like it, but financially I can just tell. And then he goes, well, you should go out there and good luck like meeting your millionaire. Like, oh, he was a little bit hurt, I think. And I said to him like. I generally didn't use to give a fuck. Like they could earn like nothing. But after paying for so much Yeah. For six years, I was just like, I can't do it again. Yeah. Like I, I don't know why I thought that money would keep me safe or something, but I felt it was just like an unconscious Well you have like a dependent and a dependent another kid. Yeah. You were like a mom in that relationship. That's what it sounds like. Yeah. So I think that like, it doesn't make me shallow, it's just based on experience. No, you don't wanna do it again. You know?

NEIL:

Yeah. Um, and also too, in a relationship, if the woman's like the mom in the relationship, it's just that's not gonna work. That's

Anna:

what I think too. Yeah. That's not gonna work. And then they, and then the guy was, feels inadequate and then he has to go cheat to make himself feel better.

NEIL:

Yeah. Yeah. That's, but you know what happens too with a guy like that, I don't know him, but what happens a lot of guys, this is before. Yeah, you're out with a pretty girl. What happens? Other girls look at the guy, oh, what does this guy have? What is it? And so his ego gets boosted and so therefore he's No, I can hit on any girl they like. To me,

Anna:

someone else told me that. Yeah, that's true. Someone else told me that, that if you are cute or you do well, you're good looking, you're out with them. Then those girls, what the guy and be like, what does he have?

DREW:

Yeah. Yeah. Pete

Anna:

Davidson.

DREW:

Yeah, Pete Davidson. I mean, come on that guy. Like no offense, but it's like he gets the hottest women. It's

Anna:

the Pete Davidson factor. He's the

DREW:

hottest women in Hollywood. Okay. Thanks

Anna:

for calling me hot boys. I'll take it. Yeah. Um, okay. Other things you have to learn though, when you're out there dating now it's all these dating terminology, like there's ton of it. Like I, I knew the basics right when I started dating. Like just the most common ones and I mentioned it before, like ghosting. I just learned about situationship, but I did not know that nano ship and the most thing and all these words I'm learning. Well, that's a good phase too. Okay, so basically I'm gonna read you a term dating terminology and you're gonna guess what it's. Here we go. Kitten fishing.

DREW:

I'm guessing it's gonna be somebody who is younger than what they said they were.

Anna:

Okay. What do you think it is? Uh,

NEIL:

she's giving away her, you know what? Much easier.

Anna:

Good guesses. Kitten fishing. A milder version of catfishing where someone misrepresents themselves. Eg. Old photos, exaggerated profile

NEIL:

descriptions. Oh yeah, that's very common. That's trying think, you know, go easy on the filters. I think for anybody, go easy on the filters.

Anna:

Go easy on the filters.

NEIL:

Yeah.

Anna:

Well, can't you tell though? I feel like you could tell. I can tell.

NEIL:

No, no. But have you seen now everyone's using AI filter. They're better. Yeah. No, but AI filter looks more cartoonish, more like, it's like it's just too much. Mm,

Anna:

too much. You know what? I will agree on that a little bit. I was on, on Andrea, I can't see women's profiles, but if I go on the map section to see just like. Symbols near me. For some reason it doesn't block out women. I kicked on some of them and I was like, I don't if these women are real. I don't stand a chance. Help look too

NEIL:

much

Anna:

now. So ai,

NEIL:

yeah,

Anna:

no, it's too much now. It, it wasn't, and then I went on a date with a guy from Raya and it was the second thing he said to me, I swiped on you because your pictures look normal. Next one, future faking. What do we think future faking can be

DREW:

somebody who's going to school to be a doctor, but they're not a doctor yet. I would say their intentions, they're lying about their intentions so they can get laid.

Anna:

Okay. A tactic often used in relationships where someone makes exaggerated promises about a shared future, such as talking about moving in together marriage or other major commitments without genuine intention of making those promises. Yeah. Every woman listening to this podcast now just kinda had a little PTSD shaky moment.

NEIL:

Okay. Have you

Anna:

done any future faking, gentlemen?

NEIL:

No, not future Faking. No. Uhuh. You never made a

Anna:

promise of like, Hey, I can't wait until the next time or next year? No. No.

NEIL:

Knowing your new intention? No. No. What ends up happening with me? The girl's like, you're not ready to get married. And they're gone. Oh. Oh, you're not ready to get married. We don't know that. Yeah, we don't know that. But right away your girls are like, are you ready to get married? And then right away. And I'm just like, well just take it one day at a time and then six months go by months, whatever. You're not ready. And they're gone. Oh, they're

Anna:

moving fast. They're moving fast.

DREW:

And in your case, drew, no. Like I never, yeah. Why lie? It's like, you know, if you see a relationship with somebody, you tell'em, or if you don't, you tell 'em.

Anna:

Soft launch. What do we think that is?

NEIL:

Uh uh, dating others while you're still dating that person and see where it goes.

DREW:

Okay. I think it's more like you pretend like your relationship, but you're really not, you're still testing the waters.

Anna:

Soft Launch used to describe the act of subtly, including a new partner in a post photo video shared online. This is a tactic often used to announce a change in a relationship status without getting into detail about a new partner. Oh, I like that. Social

NEIL:

media.

Anna:

That's cute. But

NEIL:

many guys do that to gain points with the girls. And you see we're taking that next step now. No, shoot for sure.

Anna:

If, if I'm with a guy and he pulls a picture on social media. Yeah. Together. Yeah. Yeah. Oh, we're in.

DREW:

Yeah,

Anna:

I mean we're in it, right? Drew?

DREW:

Just so much pressure. Like now, social media.

Anna:

Okay. I thi Did you learn something today? I think you did. Yeah. Yeah, yeah.

DREW:

I knew. No, none of those terms. Yeah.

Anna:

I don't know if these lost boys were found, but, um, okay. We're at the very end. We have something called the perfect 10. We end with 10 quick questions, kind of quick fire because we like to think that our guests are tens Oh. No matter what. Thank you. You've been perfect. You've been a lot of fun. Sarah, if I missed something, let me know. You feel good? Alright. So I'll ask you one question and we can go kneel first and then Drew and, and these are like little quick ones. Here we go. What is the most romantic gesture someone has ever done for you?

NEIL:

Made an amazing meal for me without me asking or anything and cleaned the house. I just get home every day's like, wow, how nice are you?

Anna:

Oh,

DREW:

drew, most romantic gestures. Uh, to me what stands out would be like, yeah, like remember like coming home one day and like just naked and was like, have your weight with me.

Anna:

Alright.

DREW:

You know?

Anna:

Okay. I think we found Drew Stein though. People have not been romantic enough around you. Maybe.

DREW:

You

NEIL:

know what, you know what? I think I, women would like flowers, but for guys, I have had some girls actually just write me a card. I was like, wow, that's so nice. You are the

Anna:

second guy to say that. Yeah. The second guy to say like, write a card. A few girls write cards to me. Another, another person got a letter. Yes. Yeah. And he loved it. Yeah. So see, we're all learning things on the show. Yeah. I've had a

NEIL:

few girls write letters to me. What's the best

Anna:

p Okay. What is the best piece of dating or love advice you have ever received?

NEIL:

Find a girl who looks up to you, kind of like a dad, like your, like your number one fan, like a girl who looks up to you.

DREW:

Oh,

NEIL:

okay. Drew,

DREW:

I'm gonna say like, actually that was your advice. Um, I'm gonna say something I read recently.

Anna:

Okay.

DREW:

Where basically I to like, I, I relate to this, like basically I. Text you right away. I call you right away in response because I care about you and I want you to know that you are important to me. Mm-hmm. And the fact that like if I text you and it takes you so long to respond or whatever shows to me that maybe I'm not as important.

Anna:

A hundred percent true. A hundred percent. A hundred percent,

DREW:

hundred

Anna:

percent

DREW:

accurate. So like, yeah. So I like, I enjoy if I text somebody Yeah. They right away engage back. Yeah.'cause I do the same thing to them. Yeah. I've like somebody, I'm like, Hey, I want you to know that like I, I'm here. I'm always there responding if I, even if it's like five minutes, I go, sorry, I was doing something. Yeah. I mean that's fair.

Anna:

I did the thing, I texted with a guy on a Monday I really liked. He asked me out for Saturday, multiple days in advance. I said, I will get back to you on Wednesday. I'll know on Wednesday I got back to him. I said, I can make Saturday work. Yeah. He then waits 24 hours to say, I think I can do whatever. And you know what? I text him back, I said, Hey, listen. Text, not text. Certainly text.

DREW:

Yeah, absolutely. And

Anna:

that is a good lesson, I think.

DREW:

Yeah, I agree. Yeah. Alright, let

Anna:

me continue. Perfect. Tap, push, push. Uh, what's the one thing you would lie about on a dating app? Ooh, when you're ready. Either one can go first. That's a DI guess you're No. Yeah,

NEIL:

no, don't, yeah, that's, that's tough. Seriously? Yeah. Yeah.

Anna:

Okay. So you, the lost person are the two most honest man. Dating, you're like a fighter.

DREW:

Like why lie?

Anna:

Okay.

DREW:

But your age is already on there. You can't lie about your age, you know? Uh, you can't lie about your age. Okay, fair, fair enough about this. I'll say that like true. I have lied about like, how long I'm in a city for.

NEIL:

Okay. We'll say this. I, I've lied. My cooking skills are great and yeah. I'm good at making rice and tuna. I'm gonna

Anna:

take it. No, it's, what is your

NEIL:

quality most

Anna:

hate or delo in a partner?

NEIL:

Try to act like a mom.

Anna:

Okay. Acts like a mom, like, uh, like boss you around like a little kid. She as a

NEIL:

boss. Or don't do this. Or, be careful. We're not gonna do that. Oh. Like once a girl does that, I'm like, you sound like my mother. You, I can't deal with this. You can't. I can't

Anna:

do that. No. I, same thing,

DREW:

bossiness. Are you close with

Anna:

your mother?

DREW:

No.

Anna:

Oh, okay. Maybe that's right.

DREW:

I would probably say the same thing. Bossiness. It's like we're, we're partners. You're not like a guy, like a mom or a boss. Like, we're supposed to be equal.

Anna:

Oh, you're both going for bossy.

DREW:

I would say bossy. Yeah. Oh,

Anna:

boss is the, is the most, let's call you most deployed.

NEIL:

I, I, I'll give you an example. Look, I have a bad habit. Sometimes I kind of bite my nails or my skin Sometimes I'm driving so it's such a bad habit's. One thing, I need a break. I went out one time with a girl. We're going out for a few months, and one day I'm driving the car. I, you know, bite my nail. She smacked my hand down.

Anna:

Oh, that's a bit much.

NEIL:

Yeah. I was just like, that

Anna:

is a mall move. Oh.

NEIL:

Like I, I, you know, I kept my cool, but I'm just like. Don't seriously, don't ever do that again.

Anna:

That's, that's, that, that's too much. Like, don't

NEIL:

ever do that again. That is too

Anna:

much. Yeah. It's okay. I agree. Yeah. You a

DREW:

partner. You don't wanna I agree.

Anna:

What turns you on? Uh,

DREW:

I love voices. Oh, that's nice.

Anna:

Yeah.

DREW:

My voices. I love voices.

Anna:

Okay. For you. Now,

NEIL:

a girl that's very, very feminine, submissive. Notice the mic. That most

Anna:

unusual place you have had sex.

NEIL:

The garage.

Anna:

Like a, like a multi parking garage.

NEIL:

Yeah. Parking. The girls like a

Anna:

multilevel. Yeah. Whoa. Okay. That's out there. So it's kind of wild. Orchid. Go ahead.

DREW:

Uh, sorry, mom. Uh, on stage,

Anna:

on stage,

DREW:

on stage,

Anna:

like a stage we worked on?

DREW:

No, like in front people, like

Anna:

on a, on a rock. Like it was like

DREW:

a sex show.

Anna:

A sex show. You had sex on a sex show.

DREW:

It was no, it was like a, like a gathering of people and they gather, would you want to have sex with that person on stage? And I was like, okay.

Anna:

Oh,

DREW:

it was like a sex convention. A

Anna:

sex convention.

DREW:

Wow.

Anna:

Mm-hmm. I would be

DREW:

too nervous. I couldn't do that.

Anna:

How many people are there?

DREW:

150. 200 people.

Anna:

150 20 people? Mm-hmm. And then they, and there's a stage to, is it a dark nightclub place? No,

DREW:

it's kind of like lit, like a, I would say it's more like a, like a, like a convention center, like a office building kind of thing. They used to ask me, would you be willing to have sex on? Yeah.

Anna:

On stage. And why wouldn't you? So Drew was like, fuck it.

DREW:

I was like, 22. And I was like, sure, let's go. And you had sex in front of all those people? Mm-hmm. And then you came and it was like, it's, it's like, no, like, it's like weird. Like they don't just sit there and watch. Like, it's kind of like you're just having sex with people. Well, they're walking around. Walking around. Wasn't in a

Anna:

zoo.

DREW:

Yeah,

Anna:

they're just like, in here we have a man having sex. Yeah. Wow. Oh

DREW:

yeah. So it wasn't like, yeah, like people just sat there and like reading popcorn, you know, it was, what is this

Anna:

place I gotta go? What is the name of

DREW:

this country? It was literally like, so the, the thing was like, you weren't, you had to be invited as a guy or girls can just go for free. So guys would have to pay, some guys would pay like 10 grand to go to these things.

Anna:

Oh God. And I was just invited more. Did you charge for this?

DREW:

No, I got in for free.

Anna:

Okay. Listen, I also,

DREW:

at 22, I was like, I got laid like, hey,

Anna:

that is, uh, that's great story. 20, but is a great story. Yeah,

DREW:

yeah,

Anna:

yeah. Have you ever sent nudes to anyone? Never. Never. Never. Yeah. You have? Yep. Uh, what's a love lesson that you have to learn twice? I,

NEIL:

I don't know if that, if this would work, but for some reason I met a few women. I thought they were divorced and they're not.

Anna:

So your love lesson is that you have to check your paperwork better on these women?

DREW:

Yes. I mean, I guess like a lesson would be like how to just like make somebody happy, I guess. Like how you learn what everybody's different. Have you learned anything

Anna:

from your past relationships you don't wanna bring into your next one? Sure.

DREW:

Like, gimme an example. I guess like everybody has insecurities.

Anna:

Yep.

DREW:

And what something I've learned is that you should let them feel less secure or insecure about those insecurities. So like more secure about it, I guess you should say. Like whatever it might be. Like if, if I like, if I'm not, if she's worried that I'm cheating on her Yep. I should then make her feel like she is the only one person for me instead of getting angry about it. You know, like for like why are you talking to that person and like, why are you going through my phone?

Anna:

Yeah. Look at this

DREW:

wrong. I should be like, well here. Like how can I make you feel more secure? Yeah.

Anna:

Hey babe, what's really wrong? Yeah. Like how can I, and you know what that is? That is like a leaps and bounds. I think that's super important. Drew, a year from today. Mm-hmm. What personal glow up. Would you and I celebrate?

DREW:

Oh, like a future telling? Mm-hmm. Oh God. Hopefully I, I have a relationship in a year.

Anna:

Aw, drew would've finally found someone in a year. Yes. And we'll toast to that.

DREW:

Yes.

Anna:

Okay.

DREW:

You finally be invited. My wedding. Hopefully.

Anna:

My goodness.

DREW:

You keep saying that

Anna:

I better be the officiate at your wedding, or I'm gonna be miffed or, or in the wedding, in the front row in some capacity. There

NEIL:

you go.

Anna:

Mm-hmm. Neil, what would be celebrating in a year?

NEIL:

You know what, the first thing I think of is career. Great. I, I just think of career and me leading in an action movie.

Anna:

Okay. So a year, just, just think of

NEIL:

career,

Anna:

we'll celebrate you leading in an action movie like Jason Statham or

NEIL:

something like that. Fine. That's what bad and love

Anna:

we do. Perfect. I love it. Love and career is how we're gonna end Peter Pan. Uh, okay. I think these lost boys are not as lost as I thought. I, I, I have hopes for them. I, uh, thank you for listening to Hey Grow you up. And the answer to that is always. Alright. Thanks Chance.

DREW:

Thank you.

Anna:

Next up on, Hey, grow you up. I won't settle. We're not picky. We're precise. Don't forget to subscribe.

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Anna Moulaison

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