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Navigating the Mid-Twenties Dating Maze

Dating in your mid-twenties sort of feels like trying to solve a Rubik's Cube blindfolded. You think you've got one side sorted, and suddenly, everything's a mess again. It's a journey where embarrassment is the co-pilot, enthusiasm is the fuel, and the occasional awkward silence is the pothole you never saw coming. 

Though the occasional meet-cutes still exist, let’s be real—it's a digital jungle out there, and swiping left or right feels like trying to make sense of a foreign language:

  • 32, but not looking for anything serious

  • 27, but in an ethically non-monogamous relationship

  • 25, looking for something short-term but maybe long-term.

Decoding these mysteries is a skill they didn't teach in school, and frankly, I’m not sure if I ever want to learn.

Even when you do hit it off with someone you like, there's still the endless loop of overthinking—which yes, has always existed in both romantic and non-romantic situations, but it feels even more heightened now. 

Did I say something weird? Should I have shared that thing about my ex? Did I laugh too loudly? Am I wearing too much perfume? Should I have slept with them so soon? Am I even a good kisser?

Suddenly, every interaction turns into a self-audit, and you're left wondering if you're just better off solo. But in this—what feels like—endless spiral, there’s always a strange crack in the clouds that comes about ever-so-often as a reminder of sorts. Yes, it feels like we’re at the end of days, but this time, at this age, has historically always been a fucking shit show. 

No one really knows where they’ll be a year from now, there’s that couple you have no clue how they’re keeping themselves alive who just got engaged, and you just ate grapes and popcorn for dinner, bon appetite!

If you talk to a parent or anyone, like, 5ish years older than you, you’ll hear them say something along the lines of:

Welcome to the era of self-discovery!!!! 

But I’ve never fully understood what this meant, because hasn’t every moment, every year, every day, been a time of self-discovery? 

When I was 8 I realized I hated beets, at 16 I discovered my love for punk, and at 22 I came to terms with the fact that I’m waaaaay more sensitive than I let on. Though I guess, I’m still…discovering.

If you’re in this same boat, use this time to get up close and personal with the true meaning of being alone, explore your preferences, and realize that every fuck up or awkward encounter becomes a story that you’ll eventually get to share with some other 20-something as a sprinkle of wisdom a decade down the line.

Though there probably won’t be a fairy-tale ending or a miraculous "aha!" moment during this time, so allow this to serve as a collective nod that none of us really have it all figured out, and chances are, things will likely fall into place eventually. Right?