Some Quick Tips on Finding Love
If you want advice about something, don’t ask someone who’s always been good. Ask someone who’s decent, but wasn’t always.
Anyone who found success at something early is either naturally gifted or got lucky, and people like that aren’t well-positioned to give advice. Often, they won’t understand what made them successful. Other times, they’ll think they do, but they’ll be wrong, which is worse.
Only those who’ve failed repeatedly at something are truly set up to counsel others. In that spirit: I moved in with my girlfriend last week after many years of singledom, and am now ready to share my hard-earned expertise with you.
Here’s what worked for me—or at least, here’s what I think worked for me.
There’s only one thing to decide on a first date: do I want to see this person one more time?
The structure of dating tends to push people into evaluation mode, which is neither fun nor romantic. There’s a reason so many relationships emerge out of situations like friendships, work, and drunken hookups, where the participants aren’t spending the whole time actively thinking about whether or not they want to date each other.
I often found it hard, on early dates, to avoid extrapolating my entire relationship with someone from an offhand comment they’d made or a snap judgment I’d formed about them. Could I really be with someone who had never heard of findom? Or with someone who hyped up the “great story” they were about to tell, then told an extremely middling story?
Evaluating people this critically an hour into knowing them isn’t a great way to make sound decisions. But on the other hand, dating is inherently a form of evaluation, which is probably why I was never able to keep myself from slipping into evaluation mode entirely. Instead, what worked for me was employing something like a harm reduction approach to evaluation: acknowledging that some of it was inevitable, and focusing on minimizing the damage. That meant reminding myself that I wasn’t trying to decide whether or not I was going to spend the rest of my life with this person, just whether or not I wanted to see them one more time. That’s a decision you actually can make well after an hour.
Have as much casual sex as possible
Pretty much everyone will tell you that lots of casual sex isn’t as fulfilling as a real partnership with someone you love. These people are right, but it still doesn’t hurt to find out for yourself and be absolutely sure. Your mileage may vary, but personally, I had a far easier time committing to someone once I’d sampled the alternative and conclusively proven to myself that it was indeed worse, no matter how appealing it might sometimes seem on the surface1.
There’s an old Chuck Klosterman essay where he quotes Steven Tyler as saying, “Having sex with the same woman a thousand times is way more interesting than having a thousand one-night stands, because the one-night stands are all the same.” Then again, Steven Tyler went through women on an industrial scale and has been accused of sexual assault multiple times since that essay came out, so I think it’s safe to say he was not practicing what he preached.
Narrow your list of non-negotiables
In my side gig as a dating app profile ghostwriter, I often encounter clients with comically long lists of requirements in a partner.
I understand where these people are coming from, but really, I think there are only three hard and fast requirements in a partner: that you have fun together, that you communicate well, and that you’re aligned on the big questions like whether or not to have kids. Everything else is potentially negotiable.
That’s not to say that you won’t end up selecting for more than those three conditions, just that it’s foolish to think you’re actually sure of what else you’re looking for. When you create a long list of attributes you desire, you’re thinking about what you, right now, want (or think that you want). But the person in most of your relationship won’t be the current you—it’ll be the series of future yous that you become over time, and who knows what they’ll want. You might have some ideas, of course, but better to think of them as hunches to be explored than true requirements.
As a friend recently said to me: “Wanting something too hard is asking for trouble. It’s unseemly to think you know what you want out of life. How could you?”2
Separate who you want to be with from who you just want to be
As my old therapist once told me, sometimes we think we want to be with someone because they have traits we want for ourselves. Occasionally this is healthy, like when an anxious person is drawn to the balance a calm person provides. But other times, misunderstanding our true desires only breeds dissatisfaction, and we don’t realize that getting closer and closer to someone who has the qualities we covet only makes the ache of not embodying those attributes ourselves that much more potent.
In the years when I wasn’t writing regularly I almost exclusively dated artists, but no amount of being near them could get me what I didn’t realize I actually wanted, which was to return to making art myself. Once I figured that out, I made better choices in dating.
Have at least one really bad breakup
Nothing will make you more careful with your drug and alcohol use than having once overdone it to the point of illness or hospitalization. Similarly, nothing will make you more determined to practice commitment and work through the hard stuff with someone than having had at least one truly horrendous breakup.
Really, really not wanting to go through something awful again makes for excellent motivation. I can’t exactly say I recommend either experience, but they do both have their benefits.
Past a certain point, the problem is you
Most people I know who are single into their thirties, my former self included, don’t end up that way because they keep getting rejected. They’re single because they struggle to meet anyone they really like. That situation is dangerous, because it can lead you to think that your problem is all these other people.
I’ll concede that it’s possible to go on ten, twenty, or even thirty dates with people you don’t like just because you got a string of bum luck. But if such a pattern continues for long enough, eventually you have to acknowledge that there’s one consistent factor in all these bad dates: your presence. Statistically, the most likely issue isn’t that the people you’re dating all suck, but rather that you’re doing something wrong: maybe you’re rushing to judgment, or selecting people poorly, or unknowingly behaving in a way that forecloses the possibility of a real connection.
It’s like the old saying goes: if you meet one asshole, they’re an asshole. But if everyone you meet is an asshole, you’re the asshole.
Wait until you’re older
I’m often envious of other couples who got to spend more of their youth together, but the truth is, I think there’s a lot to be said for falling in love when you’re older. (Disclaimer: I am 34, which I know isn’t that old, but it is well above the average coupling-up age—even in New York, the arrested development capital of the world.)
When you meet someone when you’re young and inexperienced, you fuck up on each other. When you meet someone when you’re older, you’ve already gotten a lot of your fucking up out of your system, on all those other people, and you get much better versions of each other. Sure, maybe you’re not quite as hot as you used to be, but that’s a worthwhile tradeoff for being less crazy and stupid.
That same old therapist used to say that sometimes instead of seeking things out you have to let them come to you. Action-oriented person that I am, I argued about this with her all the time. But maybe she was right. When I was single, the wait often seemed interminable, but looking back now, it doesn’t seem like it was actually all that long at all.
There’s only one thing in this world better than love: likes. If you liked this piece, could you let me know by giving the heart button at the bottom a tap? You might also enjoy some of my other pieces about dating and romance:
An old girlfriend once remarked that I never missed an opportunity in my writing to remind the reader that I’ve had sex. I apologize for proving her right.
After I said, in response, “That’s a great line,” this friend said, “You’re going to put it in your newsletter now, aren’t you?”