I've Tried Every Dating Strategy Out There & I'm Still Single

Q: How do you trust your approach to dating when you don't love the results? I'm 27 and feel like I'm finally hitting my stride with dating in a big city. It's easy meeting new people and I actually enjoy the shared awkwardness of a first date. Plus, I have a great circle of friends whom I can turn to for support and share a laugh with about the tough moments. But lately, it feels like an endless string of sending or receiving some version of that timeless text: "It's been great getting to know you, but I'm just not feeling a romantic connection." Sometimes, it ends after three dates or three months, but it always ends.

I'm sure at this point you're ready to cue up the world's smallest violin. I've read stories in this column from folks who are facing bigger challenges and WAY more difficult circumstances and doing it with a courage and strength that inspires me every week. But I've tried dates where we go small with drinks or go big with a Barbenheimer double feature. I've slept with someone on the first date and waited until the fifth date. My friends still tease me because I love taking people to the aquarium. It's my happy place! Long story short, I don't feel like I'm doing anything wrong in my love life. But how do I accept that I can be dating the "right" way without having any control over what happens? How will I know when it's time to consider changing things up?

A: My college roommate Shelby taught me a wonderful phrase: Your biggest problem is your biggest problem. I’m not suggesting that your dating situation is tantamount to grieving the death of a parent or having your city destroyed by wildfire. But it is a real problem! There are no small violins from me! It’s normal to be frustrated by dating, and venting about it often provides relief. Leave stoicism for Marcus Aurelius, OK?

I think maybe you aren’t giving yourself enough credit, or that you’re not fully appreciating how much of being partnered up is luck and timing.

Dating is frustrating as h*ll and it’s easy to feel like the outcomes are reflective of you or your worth. They aren’t! But it’s also pretty hard to not feel bad or take it personally when something doesn’t work out or a person doesn’t want to keep dating. The truth is: you aren’t doing anything wrong.

Partnered-up people are not doing life better than you.

I think a lot of people want to guide the dating process along. They want results. Or at least to feel like they can do something. But there’s not much to do! That doesn’t, however, mean you’re f*cked. Imagine yourself less as out to sea in a life raft with no hope of rescue. Instead, you’re in an innertube on a lazy river. You will get to where you’re going; you don’t need to steer the boat.

The secret is that there Is. No. Good. Dating. Strategy. None at all! There isn't one! It’s one of the few areas of life where the results are not at all proportional to the amount of “effort” or time you put in. Which is a bummer! And can drive anyone a little banana pancakes!

It’s so natural to compare ourselves to people around us, especially people who have some part of the life we want. I’m not asking you to somehow turn off that instinct, but rather to remind yourself that partnered-up people are not doing life better than you. They didn’t win some game earlier. They aren’t worth more. Who finds a connection and when is entirely arbitrary. It’s easy to come up with stories as to why someone else has found a relationship and you haven’t, but those explanations probably aren’t true.

I don’t think you need to entirely scrap your current version of dating — again, it sounds like you’re enjoying parts of it! What about mixing things up with a new app? There’s Thursday, which is only open on (you guessed it) Thursdays, and you go out with your matches that very night. If you’re into kink or non-monogamy, try Feeld. Or stick to your current app but change up your profile! Highlight different sides of your personality and swap in new photos. If you’re stuck on what to write, ask your friends for ideas — they’ll certainly know what’s great about you! If you’re intrigued by meeting people IRL, give speed-dating a whirl. (If you’re in New York, try Ambyr Club.)

If I were to somehow magically tell you that you’ll find a partner in 17 months, what would you do with that time? How can you savor your solo era?

Alternatively, you could take a break from actively pursuing a relationship for a month or three and see how you feel — more peaceful? More lonely? More bored? If you were having more fun dating, go back to it! If you wind up happier, keep the break going. This isn’t a romance ban — if someone asks you out, feel free to say yes — but rather, it’s more about letting go of the effort you’re putting in. What would that feel like?

It's very likely that at some point in the future, you will not be single. What will you miss about this chapter of your life? Because the truth of the matter is that time will pass no matter what. If I were to somehow magically tell you that you’ll find a partner in 17 months, what would you do with that time? How can you savor your solo era? What would feel the most meaningful, exciting, nourishing, and satisfying?

I say that while very conscious that a lot of coupled-up people say some version of, “Have fun being single!!!!! It’s so great!!” I am not saying that. I’m just reminding you that you really can’t hurry love, and there are reasons you might not want to.

There is no strategy. There is luck and circumstance and that’s it.

I’m also encouraging you to not second-guess yourself simply because you haven’t found a partner. The fact that it hasn’t worked out with these people isn’t a string of failures, but rather a series of successes. If you’re up for a corny (and possibly apocryphal) quote from a reportedly not-great guy, Thomas Edison is reported to have said “I have not failed 10,000 times — I’ve successfully found 10,000 ways that will not work.” You have found people who won’t work. Great! Now you know!

That doesn’t mean you were a fool for trying. If you instinctively knew whom to date, you’d go date them! Remember, there is no process here. There is no strategy. There is luck and circumstance and that’s it.

Think of dating like walking along a beach with a metal detector. Sure, if you spend more time on the beach, you might find more scraps, but if you want to find something really, really valuable, you need to be in the right place at the right time. And there’s very little you can do to make that happen. You’re just going to get lucky someday.

P.S. The aquarium sounds amazing. Really hoping for a rom-com moment where you keep taking dates there until the head marine biologist decides to ask you out themselves!

It’s A Pleasure appears here every other Thursday. If you have a sex, dating, or relationship question, fill out this form.