Is it worth it?
On dating burnout, pleasure, and the surprisingly difficult question of what we’re doing all this for.
I don’t often share my dating advice column in this newsletter, but every so often a question arrives that I think is worth exploring.
This week’s question starts as “I’m burned out on dating,” but is actually about something bigger that many of us wrestle with.
How do you know when to keep going—and when it’s time to change course?
How do you know when something that’s supposed to be worth it... stops feeling worth it? And how do you tell the difference between needing more perseverance and needing a different approach?
I'd love to hear where you landed on this one. Have you ever taken a break from something—not because you hated it, but because it stopped feeling nourishing? Hit reply or leave a comment. And if this resonates, smash the ❤️ so I know to share more stuff like this.
Dear Anna,
I’m a 36-year-old guy who’s been single for a few years, and lately I’ve started wondering whether I actually like dating anymore—or whether I’m just doing it because it feels like I should and because that’s the dominant narrative, the thing I’ve been told to do. It’s not that I can’t get dates. I go on enough of them. The women are perfectly lovely. Conversation is generally good. Sometimes they even turn into sex, which is great. And that’s part of what’s confusing me: I keep having experiences that, on paper, should be enjoyable, but increasingly I’m walking away feeling meh. Vaguely depleted. The next morning I find myself thinking, “Was that actually worth all the effort?” And the answer tends to be “not really.”
I don’t mean to sound cynical or ungrateful. I don’t think I’m depressed. I still enjoy my friends, my hobbies, my work. It’s just dating that feels like it’s become a high-input, low-return activity. Part of me wonders if I need to push through this because relationships take effort and maybe I’m expecting too much. Another part wonders if I’m trying to force myself to enjoy something that’s become more obligation than pleasure. How do you tell the difference between a slump that you shouldn’t overreact to and a genuine signal that it’s time to step away for a while?—Running On Empty
