How We All Screw Up Valentine’s Day, Year After Year

On Man Up, therapist Lori Gottlieb talked to Aymann Ismail about the actual importance of the day—and the day to day.

A drugstore teddy bear holding a heart.
Photo illustration by Slate. Photo by sergeyskleznev/iStock/Getty Images Plus.

On a recent episode of Man Up, Aymann Ismail talked to Lori Gottlieb, a psychotherapist and author of the Atlantic’s Dear Therapist column, about Valentine’s Day—and why so many men struggle to get it right. Gottlieb explained why the day really does matter and offered some advice for making it special. This transcript of their conversation has been condensed and edited for clarity.

Aymann Ismail: Is Valentine’s Day just horrible? Should it just go away because of the pressure that it puts on couples?

Lori Gottlieb: I think what’s more important is what happens in the day to day than what happens on a specific day. It often leads to disappointment because people’s expectations were not met, and a lot of times, these expectations were not communicated. They thought that their partner would telepathically know exactly what they wanted. So I think that it’s really important to understand how you guys want to spend Valentine’s Day together and to really be in tune with what your partner does and also does not want. Sometimes people do something extravagant, and the other person feels like, Ooh, I really didn’t want to do that. What I really wanted to do on Valentine’s Day was to stay home and have a romantic dinner. And now they’re being dragged out on the town, and they didn’t want to do that.

Yeah. So it sounds like you think Valentine’s Day doesn’t matter in—

No, I don’t think it doesn’t matter. I think it does matter to a lot of people, but I think that if you’re just doing some grand romantic gesture on Valentine’s Day, but the rest of the year you don’t show each other how much you love and appreciate one another, then Valentine’s Day doesn’t really feel important. I think it’s important for most people, because it makes us step aside and say, “Hey, I really want to pay attention to this. Maybe I’ve been busy at work, maybe I’ve been distracted, maybe I haven’t told you this,” and it really helps people to focus on “Oh, I need to take this opportunity to make sure that I’m communicating to you how important you are to me.”

Yeah. There’s also a lot of pressure coming from outside. I would hate for my partner to feel like she’s been missing out on something. So that’s the only reason why I take Valentine’s Day seriously—I’m terrified of her riding the subway and sitting next to someone who has a thousand roses and she has none.

Right. I think it’s really important that the person that you care about makes sure that that gets communicated on a day that’s dedicated to that. Yes, absolutely.

So I wonder if you have any hacks. Are there ways that men who have trouble showing intimacy, are there easy ways for them to get into the habit of showing it more often or more clearly?

First of all, I think that’s a stereotype. I think that so many of the men that I see will say, “I can’t tell my partner this, but I really wish I had this in my relationship.” I think it’s really important. One hack—it’s very much common sense—is talk to your partner about what you want and what you need, too. So many men are afraid to do that. They would rather eat glass than have that conversation.

[Laughs.] Thank you for that visual. For people who are listening and at home and maybe have no idea what to do for Valentine’s Day, I wonder if there’s something that is easy and actionable that people can try.

Yeah. Something that’s personal between them is always much more impactful on Valentine’s Day than just, like, “Here’s your generic flowers.”

Or drugstore teddy bears.

Right, right. Something personal, and I don’t just mean in terms of a gift—I mean just something to say, “I see you. You’re important to me.” I know people on Valentine’s Day have done things like, in one case, the woman really wanted to do this dance thing, and he was like, “I’m never doing that,” and yet he took her to that place and they did it. They both had the best time.

Wow, that’s so cute.

Other people will do something really extravagant, like a hot air balloon. Right? Whatever. Sometimes these experiences say much more than the flowers and the teddy bear.

Yeah. Just make sure that your partner doesn’t have vertigo or a fear of heights before you take them on a hot air balloon.

Right. It has to be something that you actually know they like, not a guess, because a lot of times, people guess wrong, and then the person has to pretend that they’re having fun and they’re not.

Oh, that’s a good way to ruin the night.

Yeah. Make sure that you know that this is something that they will really enjoy.

Yeah. Well, here’s a very romantic gesture that I’ve done that seems so simple, but my wife goes crazy for it. If I physically hold up my phone, power it down, and then put it in my jacket and hang my jacket up, she goes crazy. That’s like the easiest thing to do, and she appreciates it so much.

I was going to say, women everywhere are swooning now to that image. Seriously. I’m not being sarcastic. That is so romantic. It says, “You are my priority.” While you’re out or whatever you’re doing, maybe you’re staying in, maybe you’re cooking dinner for that person, and that is the gift that they want—whatever you’re doing, it’s making sure that you guys are connected. It’s not just “Here’s your gift” or “Here’s this experience,” but are you guys connected that night? Are you both feeling loved? Are you both feeling that glow? I think that’s what everybody wants: “I see you. I hear you. I chose you. I choose you.” However you communicate that.

To hear the entire episode, subscribe to Man Up on Apple Podcasts, Stitcher, Spotify, or wherever you get your podcasts. Look for the episode “Why Valentine’s Day Is a Scramble for So Many Men.”