Things I Wish I Would’ve Done Differently While Dating In My 20s

Things I Wish I Would've Done Differently While Dating In My 20s

Sleepwalking through your twenties is a difficult thing to avoid doing. You likely hate your job. You probably deactivated your personal finance app because it was a constant reminder of how poor you are. And you probably miss the days when a first “date” began with, “Do you want to go upstairs and check out my fish tank?”

There’s always pressure to get ahead professionally, but there’s even more pressure to lock someone down, make your Instagram debut after two months of kind-of dating, move in together, and live happily ever after while wearing matching sweaters in your Christmas card photo.

But it’s not that easy.

There are better-looking people with better jobs. There are endless dating apps that you constantly believe you’re too good for. And there’s the constant fear of dread that you’re going to be single forever. Which is why it’s important to take a step back and realize, “Okay, don’t freak out, everyone goes through this nightmare,” before re-strategizing.

Luckily for me, I’m no longer single. But shit. There’s a lot I would’ve done differently.

Texted back faster.

No, this has nothing to do with not “playing the game.” Winning the text battle is debatably more fun than, oh, I don’t know… pretty much anything in relationships ever.

But at the end of the day, waiting an hour to text back when I could’ve tortured them with a simple twenty minutes probably wasn’t the move. It set the standard for receiving a text back much too high and probably kept me up after midnight more often than I’d like to admit.

Still, don’t regret “tossing out a read receipt and then falling asleep for the night” though. Just a classic move.

Been more willing to go on dates with girls ‘not my type.’

What’s the worst that could’ve possibly happened? I ended up talking to a girl-who-would-eventually-just-be-a-friend and said goodbye at the end of the night? That’s pretty much what I was doing when I was out anyway. The only difference was that it was expected that I pay for both of our drinks.

Dates are fun, but first dates? Ugh, they’re the best. Yes, it’s true that I’ve never been on a truly terrible one, but maybe I needed a few that went south just to keep me honest. Maybe if I would’ve started to “go to the bathroom” just before the check came, I could’ve gotten some free draft beers out of it.

Hung out with fewer girl friends (not girlfriends).

Well, at least in public. Alone. With literally no one else around. Because you know what vibe that put out to literally every other single girl in my general vicinity? “That guy is in a full-blown relationship.” And that is not a stink you want to put on yourself when you’re single.


It would’ve been more prudent to invite another party along. Well, not another couple because that screams “double date,” but at least another guy to put out the “maybe she’s dating him and not him” vibe. Sometimes the best ability is availability so if you’re not posted up at the bar putting out the vibe because you’re listening to your friend drone on about being single, well, you’re taking yourself out of the game. Sports references. No big deal.

Put less stock in dating apps.

That’s not to say dating apps weren’t both fun and useful. They were both. But while I sat at the bar casually swiping in between conversations with friends that I’d already checked out of, I was just looking at Tinder bots and screens that said, “There’s no one left in your area.” Both depressing, both red flags.

You get to a point where dating apps seem like the only option when, in reality, complimenting the sweater of the girl in the bread aisle is probably much more of a productive way to create a spark. Yeah, she’ll probably text her friends, “OMG, this creep totally just hit on me in the bread aisle,” but it’s a better look than staring at your phone in the middle of a busy restaurant all night.

Put less pressure on the entire situation.

Finding someone to spend the rest of your life with is more difficult than landing your dream job. Fact. So when you’re single and watching every newsfeed around you get filled with engagement photos and “this one” captions, you’re pretty much thinking, “Fuck, this better go well or I’m going to have to make one of those let’s-get-married-if-we’re-both-single-at-40” pacts with your ugly friend.

Just like not every first date is going to turn into a full-blown relationship, not every trip to the store is going to end with a meet-cute. Unless you see a girl in a cute sweater who’s just as desperate as you are.

Image via YouTube

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Will deFries (Twitter / Instagram) is a Senior Editor at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram).

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