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

Dear ROE,

This is such a good question. And let’s be brutally honest here — a lot of the time, dating isn’t fun. It’s work. Unpaid work! Unpaid work that you often have to spend a lot of money and effort on! Even at its very best, dating isn’t intrinsically pleasurable in the same way that other, low-effort activities are, like eating ice cream or watching your favorite show.

So why bother?

Well, because dating is instrumental. Most people date because they hope it leads to companionship, partnership, sex, family, adventure, health insurance, a Costco Gold membership or simply a richer life. If your why for dating has gone fuzzy, the process can easily feel like crappy administrative work. So let’s dig a lil deeper on that front.

One of the most useful questions I’ve learned to ask myself about whether certain experiences are worth it, isn’t, “Did I have fun?” But: “Am I glad I did that?” Those aren’t always the same thing.

Some of the most worthwhile things in life aren’t especially pleasurable in the moment. Exercising comes to mind. Eating healthfully. Meditating. Cleaning the house so you can have friends over without being embarrassed. Caring for kids or aging parents. Getting diarrhea on that magical trip to Bali. Writing a book. Building a career. Even falling in love, which many consider the peak of human experience, can involve a shocking amount of logistics, effort, fear, pain, rejection and uncertainty.

But afterward, you feel expanded. More alive. More connected to yourself or to your fellow humans. Reading your letter, what strikes me isn’t that you’re no longer enjoying dating. It’s that dating no longer seems to be giving you anything that feels nourishing enough to justify the energy you’re putting into it. And that’s worth paying attention to.

I think we often divide experiences into “good” and “bad,” when a more useful distinction is “energizing” and “depleting.”

Some dates go nowhere but still leave you with a funny story, a new perspective, a great restaurant you hadn’t tried before, or the pleasant feeling of having met another interesting human being and connecting with them for a little while. That’s energy.

Some dates are objectively “successful” (though unpacking that word would be another column unto itself) — a good conversation, good kissing or sex, plans to meet again — and somehow still leave you feeling like your life battery is stuck at 9%. That’s depleting.

The temptation is to immediately diagnose it. Maybe you’re burned out. Maybe you’re secretly avoidant. Maybe the gamification of online dating (and of everything!) has broken your brain or spirit. Maybe you’re just getting older and therefore less tolerant of other people’s BS.

Maybe. Or maybe you’ve simply reached a point where you’re spending your energy in ways that no longer fit the life you’re trying to build. In other words, maybe the process has eclipsed the purpose.

To that end, a break can certainly be useful. If something is draining you, then by all means, do or try something that’s not that! Give yourself permission to stop optimizing your love life for a couple of months. Delete the apps. Reclaim the hours lost by doing things you find pleasurable just for the sake of it and nothing else. Notice what happens to your energy when you’re no longer constantly evaluating strangers and making yourself available to be evaluated in return.

Then, during this hiatus, take notes. Do you miss anything? Intimacy? Flirting? Physical touch? Shared novelty? The hope of meeting someone exciting? Or do you find that your life is pretty darn good as it is?

And if you do miss it, get specific. What do you miss? Not dating as a category, but the thing you hoped dating would give you. Maybe it’s affection. Maybe it’s having someone to cook dinner with on a Tuesday. Maybe it’s feeling desired. Maybe it’s building a family. Maybe it’s simply sharing your life with another witness. Those answers matter, because they can tell you whether dating is actually the best route to meeting that need — or whether there are other ways to cultivate more of it right now.

And if, after a real break, you find yourself wanting to date again, I’d encourage you to date differently instead of simply dating less. Fewer first dates. More selective swiping. More opportunities to meet people through shared interests vs. apps. More attention to whether someone makes you curious rather than merely available.

Pleasure isn’t just about enjoyment, though it can be that. It’s also about whether something leaves you feeling more yourself than you were before. If dating has stopped doing that, don’t force yourself to keep feeding the machine.

The goal isn’t to win at dating. The goal is to build a life you actually enjoy living — and invite someone into it when the invitation feels like a joy rather than another item on your to-do list.

Maybe that’s the real test. Not whether every date is fun. Not even whether every date goes somewhere. But whether, taken together, the way you’re dating leaves you glad you’re spending your finite time on Earth this way.

If the answer is no, the solution is probably not to try harder. It’s to remember what all this effort is in service of — and whether the way you're living is actually moving you toward that life. Or away from it.

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