What It’s Like Getting Back Into the Dating Game in Your Late 20s

Remember what it was like to go on a first date in your early 20s?

Splitting coconut rum fishbowls at Boston Pizza, holding hands at the movies during “Superbad,” or spooning while listening to The Fray in a stale basement apartment. It was basically a modern fairytale. 

You’d talk about who you wanted to be when you “grew up” and the inspiring documentaries that you watched on this cool new thing called Netflix. Conversations were slow and simple, because after all, time was on your side.

But since returning to single life in my late 20s, I’ve realized the game has changed entirely.

Looking back at dating in my early 20s seems like a series of exhibition games. And now that I’m approaching 30, sh*t is getting real. This is the playoffs – players keep score and it’s a race against the clock to win.

First dates in my late 20s now feel like an intrusive round of interrogation ping-pong. Do you rent or own? Where do you work? Do you want kids? How much money do you make? Any student debt? Are you an only child? Are your parents divorced? And most of these questions are fired off before the mozzarella sticks even arrive at the table.

I get why having prerequisites are important. As grown adults there’s more at risk than just your heart. Anyone who’s been burned by the demise of a long-term relationship will confirm you not only lose a partner, you might also lose your couch, your cat, your home, your sense of self…and, God forbid, your Phil Collins record collection.

Which makes choosing your next companion more surgical, measured, practical – and yet, immediate. Those little hands on the biological clock can put you in a choke hold. And I’m not convinced that people make the best decisions while short of breath.

But like anything, dating gets easier with practice.

When my relationship began, Facebook was just getting off the ground. Seven years later I was catapulted into single life, alien to Tinder, Bumble, POF and all of the new virtual dating rules. Instagram was no longer a photo album of your dog, it was an opportunity to market your single fabulous life, in a warm Valencia filter.

Like a fish out of water, my confidence was shaky, and it took several ounces of liquid courage, forceful friends, right swipes, double dates and bad decisions to finally find my sea legs.

But the most important advice I can give to anyone getting back into the game is to play by your rules. That, and stay away from coconut rum fishbowls – they’ll get ya’.