the agony of eros: dating

Helen Frankenthaler, Madame Butterfly, 2000

This is the first post in a series where I explore how love hurts and why. I’ve been in a relationship for a while, but before that I dated for several years and experienced it both as 1) really fun and 2) terrible psychological torment. Lately dating videos on TikTok, Rethinking Sex by Christine Emba, this post by Oliver Traldi, The Agony of Eros by Byung-Chul Han, and Why Love Hurts by Eva Illouz have made me think about why people seem to find the modern dating market so unsatisfying.

I’ve noticed that most people have a hard time 1) optimizing for and 2) implicitly/explicitly asking for what they actually want. Here’s my perception of how dating works for most (heteronormative, I’m not claiming to have insight into anything else) people in their 20s:

1. You use Hinge/Raya or serendipitously meet someone cute at party.

2. You go on a first date, probably at a cafe, a bar, or dinner, and talk to the person for 1 to 4 hours. You learn about shared interests, job, which college they went to, their friend group. You may or may not learn what they’re “looking for.” If given, the description of what they want usually falls into one of three categories, with the third being the most common—1) I’m not looking for something serious 2) I’m looking for a serious partner and 3) what I’m looking for changes depending on how much I like you, let’s wait and see.

3. Given that you’re both attracted to each other, you might kiss on the first or the second date. Given that you match the social norms of my friend group (interested in spirituality but not religious) you will have sex sometime between the first and sixth date.

4. You’ll see the person somewhere between once a week to 4x a week. Frequency, the type of date (is it coming-over-at-10-PM or ice skating followed by a medium-nice dinner?), and your respective enthusiasm displayed while texting/scheduling signals your level of interest and seriousness

5. At some point, either because it naturally feels right or because you can’t wait any longer, one of you will bring up the “What do you want from this?” conversation.

6. It is normal and acceptable for the person to break things off without explanation or even ghost you at any point before there’s a verbal commitment (“Let’s be exclusive or you’re my boyfriend/girlfriend”). After there is a verbal commitment there is an expectation of a conversation when breaking up.

Here are some of the ways these norms cause suffering:

1. On TikTok, women in particular complain that men signal emotional seriousness that they don’t actually feel (he said he wanted to introduce me to his family, I met all of his friends, but he still ghosted me a month in), possibly because they want sex/intimacy without commitment.

2. When someone is not communicative about their desires, the other person often doesn’t have the communication skills to ask what’s going on, and instead spends lots of time wondering about their motivations (she didn’t text me back, does that mean she’s not interested or she’s just busy? He says he’s not looking for something serious because he just came out of a long-term relationship, but we’ve been hanging out five times a week).

3. Related but separate from 2): people are often afraid of saying what they actually want because they’re afraid of coming off as desperate or clingy (I really like this person, but I’m scared that if I tell them they’ll be like “whoa, this is too much too soon”).

4. Exclusivity is rarely presumed in the early stages of dating, and any highly desirable potential partner has lots of optionality, so you’ll likely be terrified the person you like will meet someone else they like more, or likes you but doesn’t like you enough to commit.

5. We expect more from our partners than ever before—we want them to be our true love, our best friend, our coparenting partner, and the person we combine our finances with. At the same time, switching costs are pretty low (if you’re not happy with your partner you can break up with them with relatively low social costs compared to any other point in history).

6. Love is a neurochemical con job, i.e. people are more delusional about dating than they are about anything else (this person clearly acts like they don’t value me, but because I’m super in love with them I’m going to convince myself that they do return my feelings and it’s only a matter of time before they start treating me with love and respect). More on this in the second post in this series, which will focus on limerence.

7. Dating is horribly unfair. Some people can be with anyone, some people can’t be with anyone they want. Most people are somewhere in the middle. Seeing the disparity can create intense resentment, and if you feel like you’re not measuring up it’s hard to get feedback on what the actual problem is. For ex, if you’re a guy you might blame your height or income, and if you’re a woman you might blame your physical attractiveness. But it’s probably a holistic issue (i.e. you’re medium attractive, but you’re super socially awkward). So maybe instead of getting plastic surgery you should work on your social skills, but obviously improving your social skills is a non-trivial multi-year pursuit, and you might not be self-aware enough to realize that’s the problem in the first place.

8. At the same time, people don’t understand that optionality in dating is very different from the ability to date successfully, i.e. you can be very attractive and therefore have a wide range of people interested in you but not have the social skills/psychological acuity to translate initial interest into a successful relationship.

Because dating is so difficult, there’s a huge market around “dating advice” for both men and women. All of the resources tend to center around following rules as a substitute for 1) having self-awareness and 2) being a good communicator. For ex, PUA advice will say, women like dominant men, so you should frame all your conversations with them in this particular way. “The Rules” type of advice will say something like, it’s important to not seem needy, so if you double text him you might as well kill yourself. Is this advice helpful? In my opinion: yes, sometimes, especially for people who struggle with understanding (admittedly opaque and frustrating) dating norms. Like, you probably shouldn’t text someone who hasn’t replied to you six times, because they might become legitimately scared of you. And it’s obviously true that women are socialized to be less assertive than men when dating, so if your strategy is to wait until a girl asks you out, that will work with a minority of women but not the majority. But the thing that’s really hard about dating is that it tends to bring out all your attachment issues, problems you’ve inherited from your parents, primal fear of rejection, etc so it’s really, really hard (basically impossible) to fake being different than you are. Anyone who’s tried to pretend they’re indifferent to someone they actually really, really like knows exactly what I mean. Your true self always slips out.

I think there are two emotional factors to dating being less awful (sorry, I don’t have enough space in this post to dive into appearance, charisma, or status lol), both of which are easier to describe than to achieve:

1. Self-awareness: how can you go after what you want if you don’t know what you want?

2. Tactful honesty. Two tweets about this:

Ava @noampomsky

playing with the idea that extreme honesty makes you more attractive if you’re already attractive and less attractive if you aren’t

Richard Ngo @RichardMCNgo

The secret to so many human interactions is: it doesn't matter what you do as long as those actions aren't coming from hidden neediness. I say "hidden" because openly and honestly acknowledging neediness is surprisingly powerful at reducing it. Sunlight is the best disinfectant.

To illustrate both 1) and 2), I’ll use the example of when to have sex. Okay, so clearly it’s true that both having sex in the bathroom of a bar the first night you meet and having sex one year into a committed relationship has produced successful marriages. But do you understand which side of the spectrum you yourself are on? My argument is that our culture doesn’t encourage people to pay attention to their feelings enough to know (self-awareness!). Most people turn to frameworks: either I’m religious, so I’ll wait until marriage, or I don’t think sex is sacred, so I guess I’m open to casual sex. But I think some of what Christine Emba writes about is that your personal emotional response to sex is actually important? And that perhaps it’s partially your partner’s responsibility to be cognizant of that but it is most your responsibility to figure out whether it makes you feel terrible? Which is hard, because we live in a culture that completely destroys people’s ability to be attuned to their emotions? Like, if you’ve ever met a poor soul who’s horribly in love with their quote-unquote friend with benefits and tries to convince you that they’re okay with the situation even though it’s obvious that they’re being psychologically tortured by it, you know what I’m describing. My dream world is one in which more people could communicate things like, I don’t want to have sex with you even though I’m attracted to you because I’m going to feel emotionally attached to you after the fact and I want to wait until I have sufficient context to understand whether you’re actually someone I want to be attached to (tactful honesty!). Oliver Traldi:

Emba is correct that there is a deep social confusion about the meaning of sex: it cannot be both a meaningless encounter we sign up for with a swipe and a high-stakes enterprise that contains the potential both for great intimacy and for deep hurt and violation.

It also seems to me that people know what they want but they rarely know what they need. As in, they have an idea of what kind of partner would be attractive to them, mostly based on some amalgamation of qualities they find sexually attractive, qualities that their social group values, and qualities that would flatter their ego. But they don’t necessarily know what a great emotional connection feels like.

Ava @noampomsky

from what I can tell most ppl have almost no sense of individual reality, no sense of agency that isn’t dependent on or in reaction to social approval

For ex: someone might say, what I want is a guy who’s athletic, has a stable job, wants to have children, good relationship with his family, is funny and emotionally aware. I don’t think lists like that are helpful, because you’re probably subconsciously filtering based on those qualities anyway. The real thing people should be actively looking for is strong emotional connection, as in: to what degree can I share who I am with this person, do they get it, how interested are they in who I am, my feelings and thoughts, can we accommodate each other’s preferences, are we good at talking. Once I asked a very happy couple how they knew they were the right for other and the woman said, Well, we were both just really good communicators. And that’s rare. And I was like, wow, it is so rare! I think what I want more than anything else is someone who’s a really phenomenal communicator. How is it that I never noticed that? And doesn't that mean I should try to become an excellent communicator? When I was in my late teens or early 20s I would sometimes be in the early stages of dating someone and feel like there was a glass wall between us, I just didn’t really get them, I didn’t know what they wanted from me, and it was so hard for me to have any clarity about who they really are. But I would be like, well, objectively this person is hot and smart and cool. So why wouldn’t I want to date them? Answer: because you can’t really talk to them, dumbass.

Some of that disconnect was due to compatibility, but some of it was due to my own bad communication. It takes so much practice to get good articulating the deep sentiment behind the shallow one. Another learning moment was when I heard an acquaintance on the phone with a girl he was seeing. She lived in a different country, and he was explaining that he thought he should cancel his upcoming visit because he’d decided that he didn’t want a serious and committed relationship with her. She said that that was fine and he should come anyway, she wanted to see him. And he said, Well, I don’t really know if we’re on the same page. I feel like you’re verbally agreeing with me but you actually hope that if I come visit you might change my mind. I was impressed by his ability to say the subtext out loud. Most of us stop at the obvious thing: she said it was fine, I like her, why shouldn’t I visit? But I think it’s only when we’re able to communicate the precise observation, the actual feeling, that we can make real progress.

But it’s hard, it’s so hard, because we’re not taught how to ask hard questions of both ourselves and others. We believe that social reality is more important than individual reality, that being with someone who makes you look good is better than being with someone who makes you feel good. And we live in a time where we have more optionality and less transparency than ever before, where changing social norms have created highly competitive marriage markets (more on this later). That is, as far as I can tell, why dating hurts.