Dating In My 20s Doesn’t Feel Like Real Dating

A few nights ago, I was sitting in a café across from someone I had matched with on a dating app. He was talking about his hobbies, and I just nodded along, listening. Technically, everything was fine. The place was nice, the conversation was okay, nothing felt awkward. But in the middle of it, I suddenly caught myself thinking, why does this feel so familiar? Like I’ve done this exact same thing before.

And honestly, it wasn’t the first time I’d felt that way. Lately, I’ve been meeting quite a few new people. Different places, different faces, but it almost always feels the same. We go through the usual questions you’re “supposed” to ask: where do you work, what are your hobbies, what do you usually do on weekends. Sometimes the conversation flows, sometimes it’s even nice. But once it’s over, it just… ends. It doesn’t really stay with me. It feels like I don’t really know them, and maybe they don’t really know me either.

After a while, I started noticing the pattern. You meet, you talk, then you go home. After that, you just go back to your own life. A few days later, you do it again with someone else. And somewhere along the way, it stopped feeling special. It just started to feel like something I do.

I used to think dating would feel different. I thought there would be curiosity, or a connection that slowly grows into something more. Something that makes you want to see that person again. But now, it mostly feels like an exchange. Like we’re just sharing information about ourselves. We both show up as the “best version” of who we are, trying to seem interesting enough, stable enough, likeable enough. But somehow, there’s still this distance that never really goes away.

Sometimes, even when we’re sitting right in front of each other, it doesn’t feel like we’re actually there. Our attention drifts, our minds wander, or we’re just not fully in it. And I guess I can’t fully blame anyone. At this stage of life, everything feels like it’s happening at once – work, plans, trying to figure things out. Maybe that’s why everything feels a bit in-between, including dating.

Somewhere along the way, I realised that maybe what felt empty wasn’t the dates themselves. Maybe it was the way I was showing up to them. And maybe, until that changes, these will just feel like ordinary meetups with the label “date.”

I’ve been trying to look at it differently now. Maybe dating in your 20s isn’t about finding something certain right away. Maybe it’s just part of the process, meeting people while also figuring yourself out at the same time.



This article is part of TSS Confessions, a weekly column where we delve into personal finance topics that are unscripted and genuine real accounts from people.