The One Piece of Advice That’s Completely Changed the Way I Date

coffee date

Recently, while chatting with a group of women on one of many topics surrounding the theme “dating is hard,” a friend offered a particularly sage bit of advice: that the best thing you can do is think more about what the other person brings to your life instead of worrying so much about how you come off to them.

At the time, I was quick to voice my agreement, acting as though this tidbit were the most obvious thing in the world. I like to think I’m secure enough that I don’t need everyone to like me, especially not random dudes on Bumble. But while I have no trouble adopting my friend’s self-assured mantra in theory, my track record tells a different story.

I don’t know about you, but my people-pleasing tendencies run deep. Even if on some level I know I’m not into someone, I’ll find myself constantly making sure I’m a good date: suggesting another drink when really I’d rather go home, exaggerating my interest in a topic just because it’s the other person’s “thing.” (See also: the Cool Girl.) Granted, you could argue that’s just baseline politeness, but when you’re giving up your valuable free time for the express purpose of determining compatibility, it’s not a great strategy. And worse, I’ve often found myself insulted when the other person doesn’t make an effort to see me again—even when I had no intention of reaching out. To reiterate: I was making myself feel crappy over people whose names I don’t even remember.

A while back, I matched with an acquaintance I’d harbored a low-level crush on for years. I had this sense that I had to “ace” the date or squander my one shot with this guy. I’ll spare you the play-by-play, but unsurprisingly, that level of pressure pretty much paralyzed any hope of being myself—or avoiding the self-inflicted emotional beating that came afterward.

Later, while giving the aforementioned wise friend the post-date recap, she’d asked me: “Well, did you actually like him?” What did she mean—hadn’t I liked him for years? Well, I hadn’t actually known him before. And if I was honest with myself, there were a number of things that had come up during dinner that didn’t really click. Huh.

Of course, this doesn’t mean I don’t try to put forward the best version of myself when I meet someone new (romantically or otherwise). But my friend essentially gave me permission to be a little more, well, selfish. Meaning: What am I getting out of this? It’s not a contest to prove I can charm the other person at all costs; it’s an opportunity to figure out, mutually, if it’s a good fit. (An obvious analogy is job interviews, another notably nerve-racking interaction that isn’t as one-sided as it’s made out to be.)

Here’s hoping I can bury the ghost of “good dates” past. But in the meantime, should we grab another drink?

The Happiest Single People I Know Follow This Dating Advice

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Carolyn Kuang-chen Stanley


From 2016-2019 Carolyn Kuang-chen Stanley held the role of Editor covering food, travel and all things nyc.
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