What questions should we be asking about Valentine’s Day?

Valentine’s Day is supposed to be about love. But for many people, it lands as pressure, performance, exclusion, or quiet disappointment. In this episode, Lynne, Dan, and Dr. Patti take a familiar cultural moment and do what we always do on Listening for the Questions: we slow it down and ask better questions.

Together, we explore what Valentine’s Day reveals about how we define love, worth, success, and belonging. We talk about the stories we inherit about romance, the commercial scripts we rarely interrogate, and the invisible hierarchies that decide which kinds of love are celebrated and which are ignored. We also ask what gets missed when love is framed as a milestone instead of a practice.

This is not an episode about how to “do” Valentine’s Day better. It’s an invitation to examine what love actually means in your life right now, who it’s for, and how curiosity might open up more honest, humane, and expansive ways of relating to ourselves and others.

Questions we explore include:

• Who is Valentine’s Day really designed for, and who gets left out?
• When does love become a performance instead of a lived experience?
• How do scarcity narratives around love shape our choices and expectations?
• What might love look like if we treated it as a verb, not a status?

Whether you love Valentine’s Day, dread it, or ignore it completely, this episode offers space to reflect without judgment and to reconnect with love as something broader, messier, and more human than a single day can hold.

Resources we found helpful when prepping for this episode:

1. All About Love by bell hooks
   A grounding exploration of love as action, ethics, and responsibility rather than fantasy or possession.
   
   
2. The Gottman Institute Relationship Research
    Evidence-based insights on what actually sustains connection, trust, and intimacy over time.
   
   
3. Esther Perel’s work on modern relationships
    Particularly her talks and writing on desire, independence, and the tension between security and freedom in love.
   
   

Available wherever you get your podcasts. 

Listening for the Questions asks better questions so we can live more honest lives, together.

Listening for the Questions is where curiosity is our compass.

Transcript

Dan 0:13

Hello, everybody. Welcome back to Listening for the Questions. My name is Dan Ward. I'm an engineer and military technologist. I'm also an author, a juggler, and a punk. And I'll just say it, I'm a romantic.

Patti 0:25

And I'm Dr. Patty Fletcher. I'm a recovering C-suite executive from Big Tech, a leadership futurist, a gender equity advocate who is bringing new narratives to the market about women who disrupt, and a best-selling author. And I don't think I am a romantic. I think I'm a realist.

Lynne 0:43

I am Lynn Cupernal. I'm a leadership coach. I'm a healthcare consultant. I'm a triathlete, and I'm a mom. Sometimes I say that in my intro, sometimes I don't, but given today's topic, I'm I'm owning it. And I have a little bit of a love-hate relationship with our topic today, which is Valentine's Day.

Dan 1:03

One of the things I love about this podcast, other than getting to spend time with you two wonderful people, is that even when we pick a topic like sandwiches or magic or a specific holiday, we always manage to come up with really interesting questions that go beyond the obvious and are anything but superficial. So happy Valentine's Day to you both. And I think the first question has to be, hey Patty, hey Lynn, will you two be my Valentine's?

Patti 1:27

Happy Valentine's Day to you, Dan. And let me answer that very directly. As fond as I am of you, I will be your Valentine only if I get a return on investment that includes some pretty awesome dark chocolate.

unknown 1:43

Okay.

Lynne 1:44

I'm in. I love a dark chocolate too. Um, but I'm really only in if we can skip over the red roses cliche and get straight to the deep stuff. Because I mean, honestly, my relationship with this day is a little bit complicated.

Dan 1:58

Well, I gotta admit, I didn't bring chocolates or flowers for anybody, uh, but I do have some pretty good questions we can talk about. So let's dive in there.

Patti 2:05

Let's get to it, right? This is a topic about love, and everybody has a strong feeling about Valentine's Day. It is everyone wants to be loved. They want to have people that they can love. And yet the big feelings about the day of love, right? This dedicated day of love, Valentine's Day, really brings out these extreme, like all for it, and so many more who just kind of roll their eyes at the topic. And, you know, it really makes me wonder why is that, right? I definitely have some strong feelings about Valentine's Day, although I love it, like you said, Lynn, right? Like complex and complicated. So why do some people love it? And why do some people hate it? And how can a day dedicated to love be so polarizing?

Lynne 2:48

Such good questions. Um, and I'm wondering if those strong polarized reactions explain why it persists as a holiday. Nobody has strong feelings about, I don't know, Arbor Day, right? I I don't even know when Arbor Day is.

Dan 3:06

Oh, Lynn, I don't know when Arbor Day is either. Uh, and Arbor Day is like a legitimately beautiful holiday, right? It's about caring for the environment. It's about going outside and planting trees. And I remember kind of loving Arbor Day when I was a kid, like in elementary school, but I don't think I've really thought about that one for years. So I wonder, what would it take to get a Valentine's Day level response around a holiday like Arbor Day?

Lynne 3:33

I don't know, actually. I know we're not answering questions. I don't know the answer to that question. Uh, and I think I'm gonna put out a fairly common position here when I say I think Valentine's Day persists as a holiday to keep the card industry afloat. Um, although when I worked in bookstores in my early 20s, the days leading up to Valentine's Day were some of our biggest sales days, which I found delightful. Um, although I've never gotten a book for Valentine's Day, hint hint, those of my loved ones out there listening, uh, I would absolutely love to. And so it leads me to wonder why are chocolates and flowers the more commonly, you know, go-to gifts. I think it said something about society, at least in the US, the view of what women want. And do women get more gifts than men on Valentine's Day? And why?

Dan 4:28

Yeah, I'm with you, Lynn. I love to give books. I love to get books. And how cool that your bookstore was busy at this time of year. So we should make that a thing. How do we make that a thing? Giving people books on Valentine's Day. I am here for that.

Patti 4:39

I love that. I don't know if there's a national book reading day, right? But I I love that. You know, you brought up the US, Lynn, and listening to both of you. I lived in the United Kingdom for quite a while and certainly did my stints in in Asia and, you know, worked all over the globe. I will say that the US is so much more commercialized around Valentine's Day. And in England, they have folks that will do things like I'll sing for a candy, right? I mean, certainly there was the cards and the chocolates and potentially the romance, but nothing, nothing like it is here. It's less performative in the other countries I've been to from a cultural perspective. And I think that's one of the challenges I, as not a cynic, but a realist. I think, what are you trying to pull over on me today if you're going to be this performative about Valentine's Day? It might be the Bostonian in me. Maybe it's because it like it feels scheduled, it feels put on, that it feels so artificial. But like, why do I have this thing that it needs to be spontaneous in order to be real? And maybe that's because, you know, my love language is more about acts of service. Um, and you know, what does that look like versus gift giving, right? That's how I appreciate being being loved. And, you know, for me, I start to think about like, what is really lost in terms of showing your love to someone when you have to calendar it, right? When the calendar gets involved. And then, you know, kind of going back to to what we were talking about when we were prepping for this show is like love is a pretty awesome thing. So why do I have such a hard time having a day dedicated to celebrating it? I don't feel pressure, but that's certainly what I hear from other people. What do you two think?

Lynne 6:20

Yes, I gosh, buddy, you asked a lot of questions there and said a lot of things. And I do think there is something to the it's the one day. And I think about the conversation we had about New Year's resolutions, right? Maybe we don't have to set them just at the new year. Let's not think that we only need to express love for people, whether we say it out loud, whether we give a card, whether we give a gift on Valentine's Day, and I do think it's that pressure of the one day that uh makes people, I can only speak for myself, but makes people feel kind of uh about it. And then I'm also thinking about this whole Hallmark holiday and how that is like an eye-rolling thing. But I mean, really, is giving people a card to say how you feel about them so terrible? Although it does also lead me to think about who benefits from the commercialization of Valentine's Day?

Dan 7:16

Ooh, Lynn, I love where you're going there. You know, our regular listeners might have noticed we love to ask that kind of question. Who benefits from the situation? And at the same time, like, is it really so bad for a company to benefit financially by encouraging people to express their feelings of affection for each other? Right? Is that something that we want to complain about? And I wonder, like, what if more companies created more holidays or more people expressed affection and gave each other chocolates or books? Would that make the world a better place or a worse place? I don't know. Maybe that's my my romantic roots coming out and showing.

Patti 7:51

And the marketer in me is like, go for it, right? I think it's it's really this um, you know, kind of question of is it transactional or is it authentic, right? And that's kind of what I hear. Everybody believes Hallmark created this for self-serving reasons, and yet we all seem to participate or get angry when we don't. But, you know, we do call it that Hallmark holiday. But is this really just another kind of massive data sink, right? Are we all forced to run the same affection.exe file at the same exact time and at least over the course of our lifetimes. Like, I don't remember a Galantine's Day or a Palentine's Day growing up, right? I had shared with you folks, and we were sharing stories about like by the time we got to high school, it was less about handing out the little cute Valentine's Day cards with the little goodie bags and sending secret roses, right? And the school I went to, everybody got the same color rose, whether you were a friend or a romantic interest or whatever. So, like, I love that part of that Valentine's Day has evolved to different kinds of love. But the Palentine's Day is a newer um concept for me. I hadn't really heard that. I did hear it from my oldest daughter, who's part of the um LGBTQ community. But like, is Palentine's Day just like a gender-neutral version? And how do you two feel about the leveling of the playing field on the day? Is it just Hallmark's opportunity to send more, sell more cards?

Dan 9:21

Yeah, you know, I think Palantine's Day is supposed to be about friendship, uh, as opposed to the Valentine's Day for romantic connections. So maybe my opening question should have been to ask both of you if you will be my Palantine's. Uh and I am told that the ace and arrow folks, uh, that's asexual and aromantic, uh, folks tend to look at Palantine's Day as just a lovely affirmation of that broader spectrum of love and friendship. So that makes me wonder, and maybe the question we should be asking here is what would it look like for all of us to like really affirm and really include the full spectrum of human relationships? Love, affection, friendship. And I can't help put my engineering hat on here a little bit and think about logistics. Are we kind of creating a peak loading problem by packing all that into a single day?

Lynne 10:09

Right, which is what we've been talking about a little bit, right? Not just one day in February. Uh I have to just I'm pausing on the pal and the gal and the val. This is maybe a time when we should have like a Gen Zer on our podcast because we're using these terms that are, I have to say it, a little bit uh anachronistic. Is that the word? Anyway, so I there's no question there. I just had to point that out. So I know Patty's gonna like this. I'm gonna bring in AI. Does this forced expression of love or this like feeling forced to express love, does it carry less data than a spontaneous one? I'm thinking, Patty, about what you were saying earlier about spontaneity. Or is it is it the effort of participating in the ritual, the gift itself?

Patti 11:01

Yeah, you know, I I think some questions I would ask there, because I have another thought too on the other side of the spectrum, is as a marketer, some of the questions that I would be asking the data right around AI is kind of what you know, you two were talking about in the beginning. We're talking about books and sales and all of that stuff, right? Like, what is driving that expression of love? When is it driving it? And who is participating in it? And that's no doubt where Palantine's Day and Galantine's Day, right, really kind of took off because people were celebrating those things. And then how are you going to use marketing to have this forced expression of love? And what if you hate Valentine's Day? That's what people hate is that being told forcibly to participate in a holiday that celebrates someone loving you and who you love, but what if you aren't in a relationship, right? Or what if you don't have a close group of friends? There's research that came out, I think it was last week, that shows, you know, we we all have this ideal that the only way to be happy is to have a big group of friends, right? Like the show friends, but most of us actually don't, especially the older in life, right? So is it just are people hating Valentine's Day because it reinforces that they don't have a community of love around them? Or, you know, what are some of the other reasons people really don't like this holiday?

Lynne 12:23

Patty, I think, I mean, I think you're on to something. I was just thinking, sitting with the, you know, what else is underneath our our discomfort or our feelings about this this holiday? And I think it's that deep feeling of being left out, right? That worry of being left out, uh, whether it's romantic love or just friends. Um, I mean, I still remember my feelings about Valentine's Day from when I was a kid. I'm grateful I was part of an era when we gave Valentine's to everybody in the class. I and I think that's still the case, or at least it was for my kids. But wow, I can also still remember, and this has been a long time ago, the thought that went into picking out which Valentine you gave to which person, uh, because they were not all created equal. And then equal analytical thought in assessing the meaning behind that the Valentine that the boy with the big brown eyes gave, which all of which leads me to wonder how do these earliest experiences of love, all forms, all forms of love, shape what we seek as adults?

Patti 13:33

I had a different experience growing up. You didn't have to give a Valentine to everybody. And it kind of reminded me of like Battle of the Network stars meets dodgeball. Like it was everything like with me growing up, you know, I'm a Gen Xer for those of our listeners who don't know that. And it we were just this generation, man. We we definitely caught some flack from the baby boomers who who raised us and raised us to be pretty tough. I think we we all have a different definition of what that could look like now, but not everybody got a Valentine. And so what we would end up doing is it became it was like a schoolyard pick, right? And definitely I remember like going, okay, who am I gonna give a Valentine to? And who's gonna get this one versus that one, right? Like, what does that look like? We didn't give candy with it like I did when with the kids, my kids grew up giving one to everyone, but it was also like we'd literally count them up and have like a competition of who got more Valentine cards. I mean, it was awful, it was terrible. And then my goodness, when we started doing the rose thing and buying the secret roses in in in school, in high school, that was even worse. I mean, I was definitely one of the losers. Yeah, I say that. I remember my freshman year, I didn't get any roses. It it changed after that. But it was like, it was like this walk of shame, right? And so maybe there's some of that around the shame component of that maybe draws people to have such strong feelings about that. But you know, for me, it was socialized very early on.

Dan 15:06

You know, I think these early experiences just end up being so influential on us. And I wonder, is is this when we learn to associate love with candy? And I'm also curious, how do we end up with two candy-based holidays that are so different? Right? I'm talking about Valentine's Day and Halloween. Like, could there be two holidays that are more different than those two and they still manage to have candy in common? Why is it whether we want to be scared or we want to be loved, we always want candy?

Lynne 15:35

Well, again, US culture we're talking about here. Um, and maybe we should start wearing costumes on how or on Valentine's Day. That might make it more fun and less stressful. Um, and maybe that's the problem with Arbor Day. There's no candy. Uh, what if we celebrated Arbor Day, which we still don't know what it is, um, by giving each other little chocolate trees or something? Would that would people love it more?

Dan 16:00

Lynn, that's a great thought. And I'm I'm wondering now, what if it's not the candy that's missing from Arbor Day? What if it's the person-to-person connection? It's that that experience of giving each other something, whether it's candy or flowers or books or trees, because there's this connection between giving and receiving gifts and feeling love, right?

Patti 16:19

You know, this whole concept about love is so interesting because, and by the way, I just have to, as a side note, thanks for that whole connection with Halloween, because I never put those two things together. It's it's crazy. So I love that. See what happens, listeners, when we listen for the questions? Um, but you know, this whole thing about love, right? And it's so it is performative, and I'm going to give someone I love, a friend, a colleague, a lover, a partner, whatever. Isn't love supposed to start with self-love? Why aren't we celebrating that on Valentine's Day? Can't we all get behind loving ourselves? Because when we love ourselves, doesn't that better us enable to love other people?

Lynne 16:59

Yes. That's a great question, Patty. I think we should sit with that one now, this Valentine's Day. And add a similar one, which is how how do we practice self-compassion around Valentine's Day? Take away some of the pressure and the expectations.

Dan 17:18

Lynn, I love where you're going with that. If we do feel weird about Valentine's Day, how do we feel less weird about it? And does that begin with feeling less weird about ourselves and accepting ourselves and loving ourselves? And then from a gender equity perspective, one of my favorite topics for this podcast, you know, we could ask about expectations when it comes to giving gifts and receiving gifts on Valentine's Day. And I have to admit, I struggled with the prep for this episode more than usual because it's kind of a fraught topic, right? So I wondered like, how do we have an honest and a curious conversation about Valentine's Day without sounding cynical or sappy or creepy? Uh, although I don't mind sounding sappy. I just don't want to sound like the other two.

Patti 18:04

I'm happy you have standards. I was listening to Dan, and you were talking about expectations, right? When it comes to giving gifts and receiving gifts. And as I was listening to your thought process there, what really struck out at me is Valentine's Day is one of those days where we're asking people to be vulnerable very openly about their feelings. And, you know, maybe it's different in a committed relationship. Some of us, I'm not saying I have, have been with people who we were romantically involved with and they forgot Valentine's Day. Um, you know, like that doesn't feel great, but you're it's such a vulnerability on both the giving and the receiving end. And is maybe that some of the challenge we have is vulnerability.

Dan 18:48

Patty, what an interesting question. And it makes me think that Halloween is about being vulnerable too, just a different type of vulnerability. So maybe that's another thing that Halloween and Valentine's Day have in common, not just candy, but but feeling vulnerable. And how did we end up with uh holidays that are both kind of exploring that that feeling of vulnerability? Like what's what's that about?

Patti 19:11

And could I tepee or egg your house if you don't give me a Valentine? Just like if you decide to jerk me instead and give me a treat for Halloween.

Lynne 19:21

Well, Patty, I 100% think you can uh TP Dan's house if you don't get a Valentine from him. But Dan, I actually I want to go back to something you said about Halloween and vulnerability. I don't see where that comes in. I I actually see Halloween is we're hiding ourselves, right? We're we're putting on a costume. Um, so connect the dots for me. Where's the where does the vulnerability come in?

Dan 19:44

Oh, great question. Uh, I guess what I was envisioning with the vulnerability on Halloween is that it's a day to be scared. And to be scared is to feel vulnerable. And maybe we address that vulnerability by also being scary by putting on a costume, but sort of the watching the scary movie or or looking at scary decorations, uh, that can introduce some feelings of vulnerability. Is it does that kind of make sense?

Lynne 20:10

Yes, yes. And I know we're mostly just listening for questions, um, but I really wanted to hear your thoughts on that. So thank you.

Dan 20:15

Yeah, that's a that's a great uh way to clarify the question.

Patti 20:18

This is why we have three people doing this this podcast, because I was just stuck on the candy level. Um, so I hope that I have some deep thinkers as friends. You know, I you know I'm gonna bring AI up. Lynn brought it up, I'm gonna bring it up. We talked a little bit on a previous episode about how in Japan a woman married an AI bot because you know she was able to create the the ideal partner that she wanted, and men because there aren't a lot of available women and young women who are in Japan, are creating relationships with AI robots. You know, it kind of makes me wonder is the next iteration of this Hallmark holiday going to be AI and asking them to be the Valentine? Like we are the last generation, Gen Gen X and older millennials to, as Benny, Mark Bennyhoff from Salesforce said, the last generation to have led human-only um workforces, right? And I would argue the last to have human-only relationships. How should we be thinking about our relationships with all the AI agents and bots that are out there that we're creating in and kind of to mirror what we want? And how does that go with love?

Lynne 21:29

I'm I'm sitting with how I felt, Patty, when you talked about AI and Valentine's Day. I I felt icky. It just made me feel like, oh, sort of sad. And I know that this episode is talking about Valentine's Day. I think there are questions we need to be asking about this epidemic of loneliness. I think we are experiencing as experiencing as a collective culture, not just in the US. And Uh, the relationships that people are forming with AI, I feel like is just hugely endemic of that. So I guess my question is: what are the questions we should be exploring about loneliness?

Dan 22:12

Yeah, I mean, if we think of Valentine's Day at its best, is a way to reduce loneliness, to build connections and share expressions of love that might otherwise go unshared or unsaid. And then at its worst, it can make the loneliness worse as people feel left out and excluded or performative. All of the things that we've talked about. So I guess maybe a question to ask is how do we do the best version of something like Valentine's Day in a way that is inclusive and welcoming and genuinely loving? And how do we avoid the harmful downside of this type of uh a holiday or this type of an activity? I again I don't have an answer for those, but but that's I think a good question to be asking. How do we make sure we're building the good version of this and not the harmful version of it?

Patti 23:02

I love that. And we know that there is power in consumerism. And ladies, you are responsible for 90% of all consumer buy decisions. So when it comes to this holiday, choose wisely, just like you would any holiday. You know, Lynn, I want to go back to something that you said about, you know, when AI comes up and this topic and having AI as your Valentine or whatever time it's going to end up being, um, how it made you feel icky. And I'm with you 100%. And Dan, as I was listening to you talk, like I wonder if that's how people who have a disdain for it and they're disguising their their vulnerability with anger, which many of us do, right? Is it because they feel icky? Right. And then I also wonder, you know, I never believe a artificial intelligence or augmented intelligence should ever replace humans. But what if you simply don't have people in your life and you need something to feel loved, right? As long as it's not replacing it, but at least kind of stop gapping. But is that so bad? And then of course it becomes what is our responsibility in feeding the beast on that, right? The beast being AI. It's it's so interesting when we think about we are in a state of, and this is not a technology episode, but we got to talk about it. We have gone from using technology to do things faster, right? And to do things, you know, for less money. It's been very transactional. And now with agentic AI and then moving forward, it really is about AI learning from us, not just in those consumer trends. I talked about as a marketer, but and beyond sentiment, it's about feelings and emotions and empathy and compassion and all of that stuff. And it's gonna be, I wonder if it's gonna be harder and harder as we get to these, like, and I love that that this is a human connection holiday, unlike Arbor Day, which we should see as human connection because you know, climate. I'm wondering like, are we are we going down a path where it's going to be hard to avoid AI in this because AI wants to learn how humans interact and feel?

Dan 25:14

Oh, terrific questions, Patty, all of them. And I'm gonna throw in kind of a hard pivot now because I just realized we're pretty far into this episode and we have not once mentioned Saint Valentine, like the guy this whole holiday was named after. So, how does that happen to have a holiday named after a person and we can spend 25 minutes or so talking about it, and his name doesn't even come up? So, what does that tell us about how our traditions and holidays change and evolve over time? Oh, Dan, I love those questions.

Lynne 25:46

Um, and you might have heard one of the legends around Valentine was that he performed secret marriage ceremonies. That's why this holiday is all about love. But did you know the reason he did those ceremonies was so married men wouldn't get drafted into the Roman army? So this was all about opposing the empire and keeping people from being shipped off to war. Also, why why am I always the one giving the history lesson?

Patti 26:16

Because I am begging you to. Um, between you and Dan, you know I love a good origin story, and I didn't know that. And you know, listening to you really got me to thinking, how do we bring more of that to this holiday, right? Forget the flowers and chocolate. Who am I kidding? I want those two. But how about we use this holiday to bring more civil disobedience to stand together for the things we love, right? Through peaceful protests. What if that is what February 14th started to look like?

Dan 26:46

Patty and Lynn, I'm just struck by how the message of Valentine's Day, uh, historically and even today, is is just so counter-cultural in our current moment, right? Where so many people are committing so many acts of violence. So, so yeah, how can we bring more of that peaceful civil disobedience to everyday life on February 14th and all the days around it?

Lynne 27:08

That is the perfect way for us to wrap up. Thank you both. Um, so before we formally close out this episode, we'll leave you with a few final questions to ponder. Starting with how do you feel about Valentine's Day? And what's underneath those feelings? And can you feel anything shifting as you as you think about it?

Dan 27:32

And then let's ask ourselves how we can bring more love into the world with our vals and our gals and our pals.

Patti 27:40

I can't help but think about Tina Turner singing into my walk bin as I was a teenager, listening. What's love got to do with it anyway? Right. And after today's episode, I gotta tell you, it turns out love has a lot to do with it. And I'm really starting to change my own mind and ask a different question is really, truly, so what is wrong with celebrating? What brings us together as humans anyway? And I just have to say, I'm gonna answer that. We need it now more than ever.

Lynne 28:14

As Anne Lamotte always says, love wins.

Dan 28:19

And as Elvis Costello saying, what's so funny about peace, love, and understanding, right? So thanks for listening, folks. Today's episode was sponsored by Love. In all its forms and functions, love. It makes the world go round.

Lynne 28:32

Our music was composed by Jake Cuppernal, who we love.

Patti 28:36

Our cover art was created by Mad's brand, who we also love.