Digital Dating: Does Tech Help or Hurt Our Chance at Love?

Dating apps have revolutionized how we meet, but in doing so, they often short-circuit the vulnerability required for real connection. After going on 25+ dates in one month, I discovered that while apps are great at generating matches, they rarely help us transition to meaningful, in-person relationships—and may even trap us in fantasy connections that never materialize. These platforms thrive on keeping us swiping, not settling down, optimizing for engagement over emotional growth. Yet, meeting face-to-face (doing the hard thing) was where I found the most value, growth... and even a few sparks. What we need now is a shift in how dating technology is designed: tools that don’t just stoke desire but support courage, presence, and the messy, beautiful work of building something real.

Transcript

Michael Tucci (00:00.162)
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Michael Tucci (00:09.391)
Hi, this is Mike and welcome back to my podcast. I am trying something a bit new today, so bear with me. This is just me, just talking about a topic that I have been focusing on recently. So the topic is relationships. And one of the things I wanna do with this

podcast, think tomorrow, is really explore how technology, the evolution of culture, of society, Western societies that I'm living in, how that is influencing the way that we do everything in our lives. And I think I'll end up focusing on

probably the core things that are important to life, right? So one of them is definitely relationships and love. And so I wanted to talk a little bit about my relationships and in particular, my love life and a little experiment that I did over the past few months, which was really to prioritize dating and using different apps, different

technologies to help me with that. mean, really, technologies. I don't want to make it sound too fancy. I mean apps. And one of the main takeaways really from this month really relates to the takeaway that I have about technology in general and the way we're using it to transform our lives and in particular the

things that it's homing in on in order to hook us, to transform us, to change the way that we approach those parts of our lives. And I think that, you know, if you think about the hierarchy of needs, right, like Maslow's hierarchy, which, you know, on the bottom, you have very base needs, like I'm actually, I'm just going to pull that up so I can not guess.

Michael Tucci (02:23.864)
Okay, so the bottom is going to have more physiological needs. So hunger, thirst, making sure you're not freezing to death. On top of that is safety. So making sure that you feel safe, you can avoid pain, avoid hunger, then it's social needs, feelings of love and belonging, and then self-esteem. So status and...

then finally self-actualization, which is higher selves. So becoming a complete version of your best self, let's say. And I think we've unsurprisingly developed technologies that tend to hook more those base needs, right? And those certainly can help us survive when we're in a life or death situation, right? Like making sure that literally survive. So like making sure that we

eat as much as possible, that we have shelter, that we have sex with as many people as possible and procreate, right? Those are base needs, which are really good for survival, but they can, especially when they're focused on solely or disproportionately, they can lead us to over-index on short-term gain at the cost of realizing some of our higher-level needs.

And I definitely, definitely find this with dating and apps. So let me dive into it. So as I said, this is an experiment. I not talking with anybody. think one of the cool things about conversations is they flow organically. You can't predict what the other person is going to say. And so you end up just having this like very

organic, more authentic dialogue, and it's fun to listen to. And in order to try to replicate that in this solo discussion, I've purposefully not over planned this. I don't know if it's going to work. I definitely, when I'm recording solo, I have a tendency to want to stop, to want to edit myself, also more read from a script. I am not doing that here, and I don't know if it's going to work, but let's try.

Michael Tucci (04:47.361)
So I wanted to start out by going a little bit through my romantic history and touching on kind of setting up where I was at when I went into this experiment of really kind of going on dates in overdrive, both pre-apps and then my experience with apps over the past decade and then leading up to this experiment. So I'm going to start.

with, I'm gay, so with coming out and really starting to try to date for the first time, which very importantly was before apps existed. I came out when I was 20 years old, at least roughly, maybe give or take a year, and it was a process of a few years really coming out to everybody. I was...

in my junior year in college when I told the first person. So I went to a very liberal university. was junior year that was, guess, 2005. And there was, you know, it's late enough in the progression of the, you know, gay rights movement and just the world being comfortable and accepting gay people that there was

definitely a gay, a noticeable gay presence on campus. And I remember going to some parties that were gay oriented and like having my first kiss, my first sexual experience. And that was great. But then I graduated and I graduated into an environment where there was no Grindr, there was no Tinder, there was no real good online tool to

connect to other gay people. And so what I found myself doing, and I would say mostly in a negative way, because I didn't really have gay friends. So I was in college in Boston. I graduated. I stayed in Boston for a year. I had some friends that were still at school, but they were focused on their university life. And I was no longer at school. And so I tried to venture out.

Michael Tucci (07:09.849)
into the broader gay world in Boston. And I had no idea where to go other than to go to gay bars and gay clubs. And so that's what I did. And for like a year, I really, I put my all into that, to the detriment of my physical and psychological health, I would say. There was a lot of going out solo to bars, dealing with the discomfort of being alone and not knowing anyone and not having a community by

drinking too much and the people I did meet, I would say that the relationships were not strong. They weren't being mediated by any other force in my life, right? There was nothing binding me to these people other than the fact that we were gay and in the same bar at the same time. didn't really share anything else in common. We often didn't have

discussions about why we share it in common because it wasn't you know, it wasn't going on dates. I was just putting myself in a physical location where other gay people were and getting drunk and hoping for the best and I would say that the best did not happen and I am I'm honestly I'm jealous of younger people now younger gay people who have two things one the benefit of visibility onto other gay people

gay culture even without having to come out yet. That was not something that I really had the benefit of. And to, you know, apps, Grindr even, but then any dating app that allows gay people on it, which I think fortunately are most of them. And I, without that, you know, I struggled to find other gay people on Mink.

connections. And so I, my first boyfriend, Greg, who I dated for a very long time for 10 years, we met because I was fed up with only meeting people in bars. knew I had an intuition that it wasn't healthy. And so I, I was, I did eventually go to business school, but this was well before I was applying to business school. HBS Harvard had a, like a gay

Michael Tucci (09:38.353)
conference or a gay event for potential applicants and really I was going to that in order to get a boyfriend or meet someone. I really, as I said, I wasn't at a moment in my life where I was actually trying to go to business school and it worked. You know, I went there. I remember there was a like

a lunch and learn session and the guy who was a current HBS student who was, there were breakout rooms and the guy that was leading this one was very cute. And then I saw this other guy, my future boyfriend, who was also very cute. And I was like, I'm going to go in that room. I did not manage to, to talk really to the, the cute leader of the group, but I did manage to sit next to this very cute guy and

We ended up chatting and we ended up spending the rest of the day together. We quickly made the connection that, and it was totally random, that one of my best friends in college was his best friend in high school. And I will say that that, you know, I mentioned just before not having any sort of like social net or network to mediate or institutions to mediate.

the relationships when I was just meeting randos out in bars, this was a comfort, right? Like I, it felt more like this is the way that these things are supposed to go. We had good friends in common that could, you know, gave you some certainty that this was a person that was my people and good people. And he was and is, and he's still a very, very good friend, even though we're not dating anymore. And

Then I was in that relationship for 10 years and I could talk about that for a very long time, but that's not the purpose of this podcast. So I'm gonna fast forward a bit and say that about that relationship that it was a good relationship, but I also think I hid behind that relationship in many ways. I had a lot of insecurities, a lot of self doubt.

Michael Tucci (12:03.993)
I really didn't like myself very much in my early twenties, which, you know, it's also another podcast in and of itself, but as many gay people who are closeted and just kind of coming to terms with being gay, I think there is a lot of pent up self-loathing and compartmentalization. And it took a long time for me to unpack and I certainly didn't have it.

unpacked when I was in the decade of that relationship. And I...

found myself after about 10 years, the relationship fell apart for a lot of reasons, but I wouldn't say they were, I think it ultimately was a bit, it was mutual and we ended on good terms and I would say that we grew apart and probably I really just needed to deal with some of this stuff that I was unpacking outside of a relationship because I was using the relationship to hide behind in ways.

And so I exited that relationship and now this was at a time, this was around, we were off again on again, let's say from 2015 to 2018. And this was a time when apps were as they are now very much in full swing, maybe even more in full swing because I think there wasn't yet some of the backlash to apps. And I will say that

apps were great. You know, I could, I, so I, I used Grindr a bit. I was, I think I was too uncomfortable with my sexuality in general to really prioritize having sex with people at that point. So it wasn't like I was going and hooking up with a lot of people on Grindr, but I was using Tinder a lot, the swiping back and forth and making these very quick connections and having this visibility onto the number of

Michael Tucci (14:09.083)
people that were out there and kind of the things that that did in my mind, right? Like it allowed me to fantasize about all of these potential partners that might be good fits and that I could get to know and fall in love with. And this is maybe a theme that will come up. I think I sort of over-indexed on that fantasy world, right? Like, and I think that's one of the...

dangerous parts of apps is that they allow you the illusion that you're doing work, that you're connecting with people, that you're getting closer to a relationship when they shield you from all of the hard stuff that you need to do to actually make those real connections. So I was spending most of my time

online, swiping and having very superficial conversations and very, very little time actually meeting people in real life. And I would say that dating felt scary, right? I imagine that in a world before apps where you would have to, I mean, as I sort of did, you have to go out to a bar and meet people. The difficult part is like,

going up to a person and especially in another era where the gender norms were different, although I think they probably stay similar in reality these days. The expectation was that in heterosexual relationships, would do the inviting, would do the hitting on. And that was probably, I'm sure still the hard part, right? Like it takes courage to walk up to somebody and...

and cold approach them, right? Or even better, you could rely on existing social networks, which I think still works for straight people, but for gay people, it's actually two interesting observations on the gay front there. One is that I think that gay culture suffers from not having these clear expectations and norms for who does the hitting on in,

Michael Tucci (16:31.937)
real world environments. And I've seen this in gay clubs many times. Like I have many friends who were very, very attractive and like I'd watch them dance alone for the bulk of most nights. And my guess is that there were many people in that bar that were attracted to them. But because it's not clear who's going to approach who, I think there's a disproportionate number of people who are not daring to approach others and

hoping that somebody else will come up to them. And so you have a critical mass of people who are in a bar, in a club, because they want to meet people. And none of them are taking the step to actually do the hard thing of approaching someone. And I think this gets obscured because there is another part of gay culture that is very masculine and sex oriented. And you do have those, I think actually really a minority of people who are going to

aggressively go after the people they like. And we tend to only talk about that, but I think there's a large contingent of people who are not daring to do that. I also think that it's harder for gay people to rely on just social networks because the percentage of gay people in any kind non-gay social network tends to be low. And it's hard

You're only going to have a few other people that are two degrees of separation away from you and the chance that you're going to be attracted to those people and they're going to have the same values as you. It happens, but it's you can't, we can't rely on it like our straight friends can. Anyway, so where was I coming with this? got a little bit lost, but yeah. So I was turning to apps to

try to meet people and not really willing to do the, or not often taking the step to meet people in real life. And so I spend like a lot of time in a bit of a fantasy world and I would, you know, I would do things that teenagers do when they're learning how to be in relationships. So I develop crushes from afar.

Michael Tucci (18:56.315)
To be fair, so there's one crush that I was living in Paris at the time and there was this guy that I saw at a running club that I joined, a gay running club, in a time where I was actually taking steps to try to move things out into the real world. So I was hiding behind apps, but I think I knew on some level that that was not something I should over-index on. I did try to meet.

people in the real world too, but as you'll see from this story, I still got kind of pulled back into this online way of doing things. And I saw this guy, I thought he was beautiful, and I stalked him online afterwards. I only met, we like exchanged names when we met at this running club, nothing more.

And I realized at some point I looked through my old Tinder matches and that we had matched and he had messaged me and I never responded. And in my defense, his photos on the app were like blurry. my guess is that he wasn't completely out and he was trying to figure out how to navigate all of this. But I ended up, you know, stalking him online. I did message him.

and did try to meet him. did not work out. We did meet many years later, but nothing significant happened, let's say, in terms of relationship. But I spent several months really developing this mental fantasy, this crush, this infatuation, you could even say, with this guy. And that was...

I would say that was the norm. That was more of my mental energy, more of my energy related to dating was going towards this fantasy existence rather than really getting out there and trying to form relationships with real people. And social media, dating apps do a good job of fueling that, right? Like we can see enough about, whereas I imagine in the past you could certainly fantasize about someone, but you

Michael Tucci (21:16.74)
they were going to be a person in your class or at your work or somewhere where you were and had to deal with them in real life and where you probably knew people in common. online, so right, like you'd be forced or you'd at least be put in a situation where it made it obvious that if you had any sort of spine, you should take action and like,

do something in the real world to try to get to know this person, to try to deepen your relationship with them. Whereas online, like the most I could do was send messages, which again I did, but there's just, there's the photos, there's the seeing friends that you have in common in a digital way, but most of those people are not gonna be, at least in my case, they're not people that I actually know super well. it's not, it's a very sort of,

Maybe the best way to say this is focus on the fact that like I was so fixated on the fact that we had matched on Tinder. saw this guy in real life. I fell for him in a superficial way. And I saw so much meaning in the fact that we had already matched on Tinder and he had pursued me. Right? Like that was proof in my mind that this was meant to be.

But in reality, it's like based on almost nothing. Like I had a bunch of matches. Like I had messages from, as I'm sure he did, from many people that I didn't really engage with. And 99 % of the people I didn't engage with in kind of meaningful way and certainly didn't meet. Anyway, I then I got into my second relationship with my boyfriend, Consti. Interestingly enough, that's also, that is

Due to apps, I was, and it's just another interesting artifact of what can happen in an age of apps. So I was on a work business trip in Munich. I was, as I said, living in Paris and I matched with this guy. We started chatting. He was very witty and funny and I was only there for a few days. So I left and we...

Michael Tucci (23:36.905)
kept in touch and we'd, I I post stories on Instagram and he'd respond to them, but we never met. And then finally I was going to be close to where he was living, which he had moved to another city in Germany. And we met and we ended up dating for a few years. Ultimately that fell apart about a year and a half ago, two years ago. And I found myself single.

I've now this will be the third episode where I mentioned the death of my brother, which for people who listen that often, thank you very much for one, but two, this is not the last time I'm gonna bring that up. And that put everything on hold. So I spent most of the past year and a half, let's say single and not focused on.

Relationships, I did this program in Barcelona early last year. I didn't go on a few dates, nothing. Didn't find anybody that I clicked super well with. And I think I also wasn't really yet mentally in a place where I was ready to explore getting into a new relationship. And then I moved to Madrid at the beginning of this year and

after spending the holidays and some good time at home and I am certainly not over, I don't believe you ever get over a traumatic death like that, but I finally felt in a place where I could prioritize dating. And so I really leaned in and this is really January and the beginning of February.

over the course of a little bit more than a month. I wish I kept detailed log, but I went on 25 plus dates with 25 different people, plus some second dates with a few of them. And I really used apps to, as a volume game, to meet as many people as possible. I, however, took the approach that I am going to force myself.

Michael Tucci (25:53.172)
to do the hard thing and meet people as quickly in person as possible. I am not going to just swipe. I am not going to have a bunch of very superficial conversations on dating apps. I'm gonna learn what it means to get over my fears and meet people in person. so firstly, and I guess I can get to some kind of takeaways from this, it worked.

It worked. I'm not in a relationship, but it worked in terms of getting me over the fear of putting myself out there. So the, and this is the last I could unpack here. I'm not going to, but my thirties have been, were marked. I'm now 40. My thirties were marked by dealing with a lot of these insecurities that I have and learning to.

It's cliche, but I'm going to say it, learning to love myself. And I think I've done a good job of that, but I would say that when I was, you know, single again, going into this year and meeting people, it would, I'd get so much anxiety before going out. So I would, and I could feel that reptilian part of my brain trying to protect me and

telling me you don't need to do this and trying to come up with excuses to prevent meeting someone who, and the fear, right, is that they're gonna judge me and they're going, they're not gonna like what they see and that's gonna hurt and that's gonna feel like rejection and abandonment. And I think the other piece of that, right, because ostensibly they've seen you online, but you're

It's photos, I did include some videos, but photos that they're seeing, you're presenting your best self, they're not really, you see people in such a different way in real life than you can ever on social media in general, but certainly on dating apps as well, that when they see the complete picture of you, they're not gonna like what they see. I, you know, for a long time I had this, I mean, this touched on a much deeper.

Michael Tucci (28:15.454)
insecurity of mine, which was I couldn't really accept any of the positives about myself. like if, and let me make this very superficial. So even talking about pictures, when I saw a picture of myself that looked good, I would discount that as being a trick of the camera of being a good angle, but that's not really what I looked like. And then any picture where I looked bad, I would say that

that's the real me. And by the way, like I actually, there's so, so often on dating profiles, see pictures of people where like five of them are good and then one is bad. And I'm like, you threw a bad picture in because you were probably thinking the same thing as me. And I, and you thought that you wanted the person to see all sides of you and not be tricked.

I actually, it's funny, I think that's a terrible strategy because, I mean, you should not be catfishing people. You should use a few good pictures that show you in a good light in sort of different facets of yourself, but don't put a bad picture in. Bad pictures are also not representative. Nobody, people when they see you in real life, they don't just catch a glimpse of a bad side of you. They...

almost immediately form a very holistic perspective of your appearance that is robust to catching you at a bad angle. But when they're flipping through pictures, they don't have that full picture yet. So like the only thing that you're doing when you put a bad picture of yourself is telling the person that maybe the full picture is gonna look bad. Anyway, I digress. So yeah, I had this fear that I...

I was that they were going to see the real me and they were going to be disappointed. And that was at the beginning of this year that was coming up again. And over time, going on this many dates, first of all, I would say that the reaction of most people was good, fortunately, and that boosted my confidence. But also there were times where the person wasn't as into me as I was into them or vice versa.

Michael Tucci (30:37.434)
And I think both of those really helped because especially when I was the one who, you I met the person in real life and I wasn't really feeling it, it wasn't like I felt they fooled me. It wasn't like I felt like they were ugly. It wasn't like I felt that they were a bad person in any sense, physically or otherwise. It was more just that, okay, like this is not the, I'm not feeling it. I'm, this is not.

somebody that's really pulling me and it was so clear that that was about not having found a fit, right? Like we're just not a good match. wasn't a judgment on them. And in realizing that I could then not being liked by others, I could take it as, okay, this just means that we're not a good match and it's not a somehow a referendum on my worthiness.

Also, in general, just doing it so many times makes it obvious that there is so many different ways that you can react and the feelings here are so complex and hard to, it's very often like an X factor that you can't really, at least I can't put my finger on exactly what is wrong with a person or exactly why I don't have a connection. It's more, it's just not there.

And that's much easier for me to deal with than I think this fear that I had, which was that there is some scale of worthiness that I was on in an absolute sense. And by either getting accepted or rejected, it would tell me where I was on that scale. And in reality, there is no scale. There's just a bunch of people judging people on a

crazy number of variables that they're not even aware of themselves. And fortunately, there's enough variety that we, I think, can all find people that we like. Anyway, so that was, it was overall a good experience for that. Why do I think of the technology? So, let me go through some of the apps. Tinder, Tinder actually ended up

Michael Tucci (33:03.262)
I think being the app that I liked the most and use the most. So swiping is incredibly fast and convenient. The fact that Tinder focuses on location is great, right? The goal should be to meet people in person as quickly as possible. And you need to be in the same physical location in order to do that.

at least to do that easily. And I, so I also used a bit, not very often, but Raya, which is this like elite app, but it's really not focused on location. So you can match with people from anywhere in the world. And they're often very beautiful people. So it's addicting. I definitely enjoyed using it, but I knew on a deep level that it was like crack.

these beautiful people were being dangled in front of me and for what? To look at them online and maybe exchange a few words, they were never in the same place as me, so I never met, haven't yet to meet any of them. I also think that Tinder gets the volume thing right, so I used Hinge as well and Hinge has a similar matching feature, but there's more rich information about

the people, there's also prompts that help you kind of start conversations. I actually think that this is the wrong direction. I don't think the problem with online dating is that people aren't good enough at having text-based conversations. I think that text-based conversations are like,

good for people that you know already and already have developed relationships with, but I think they're a terrible way to get to know people. And, you know, I think some of the apps, I didn't do this at all. Some of the apps have like added Tinder definitely has like a video feature. I never use that. That's for me. It's probably a good idea. It's just weird. I also don't like meeting people or video. I want to see you in real life. And anyway, the broad takeaway is that a

Michael Tucci (35:25.492)
good dating app experience is one that allows you to play, like I think they're great at the volume game. So you get to just see people, a lot of people quickly and make some snap judgments, which to be honest, that's what you do in real life too. And you're walking down the street and you see people and you're like, I would definitely have a conversation with him and probably not him for romantic reasons. And

It gives you a very sort of low cost way to see if there's mutual interest. After that, I don't think you need to worry too much about whether you can text well with each other. I think you just need to meet in person. And this is where I don't think any app does it well. So Hinge kind of tries to do this by limiting the number of people you can talk to.

at a time, right? Like you need to respond to people's messages or you can't match with other people, which feels much too much like a stick rather than a carrot. I actually hate it. And I would tend to stop using hinge just because I would be like, I don't want to respond to this person. And now I can't match with anyone.

I don't think any does a real good job of helping you transition into the real world. And I am aware that this is at least partially because they don't really have an incentive to do that. They want to keep you on the app. And I'm not sure, it's beyond the scope of this discussion to figure out how to align those incentives. But I think that if somebody cracked that, that would be good.

as I said up front, this is one of the things that I think we need to solve with the technologies we're developing. So often they rely on that base instinct, right? Like just seeing, in this case, it's seeing people you're attracted to and like feeling the dopamine rush of like matching with them and having a connection with some of them. And then the only other thing it's really

Michael Tucci (37:41.318)
optimizing for is its own sort of capitalist incentive to keep you on there, keep you engaged, keep you spending money. And there's no balancing of is this actually helping people achieve their goal of finding love, of making meaningful connections, of even meeting in the real world. And I

Refuse to believe that's impossible. It's actually, it's very, I'm never asked any questions or there's no, it doesn't seem like these apps are. So Hinge will ask you if you've met somebody and what you thought of them. And they're clear that they're not going to communicate this to the other person, but Tinder doesn't do anything like that. And there's no other data that they're, that I can see that they're collecting on the full

breath of this experience, know, not just am I engaged and staying on the app, not just am I swiping and getting those dopamine hits, but is this helping me achieve any of my higher order goals? And I think it's possible. I don't think that that's, I think that's a choice. And I think we need to build apps and technology that help us do it, that help us, in this case, it would be really the critical.

piece for me is help make it easier for people to meet in the real world. also imagine that they could hold hands potentially a little bit more as the in the early stages of the relationship, like figure helping people figure out if somebody is a good match for them, helping people. I mean, right? Like what is swiping? But just seeing if there's mutual interest, you could easily do the same for a second date. Like why is no one doing that?

Yeah, I think maybe I'll end it there. I'll just say this. So dating apps help me connect with people. I think they help connect people, yes. I think in a digital sense, they don't help people connect physically and they don't help people connect vulnerably.

Michael Tucci (40:09.01)
And that's what's needed for deeper connections. They help with the volume of the number of people you connect with, but they don't help with vulnerability and difficulty of putting yourself out there and forming, meeting a person, which I think is, there's no substitute for that yet, and forming deeper relationships.

And I think that's a solvable problem, and I hope that there are some people out there solving it. Anyway, thank you very much.