How to Be Single In Your 20s: 4 Dating Tips for My Niece

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Six months ago, my best friend had a baby, a cute little muffin of a human named Jane. I have since found myself in the habit of babysitting Jane most Saturday mornings. Now, allow me to be bold: Babysitting has never been my jam, you feel me? I did a lifetime’s worth of the stuff back in high school: Changed enough diapers to fill a bathtub; spoon-fed enough hotdogs to build, oh I don’t know, a highchair.

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I’d hoped those days were behind me. But then my best friend — bleary-eyed, milk-stained, and sweat-pant-clad — asked me for the favor.

“Pleeeease,” she begged. Her hair was styled to suggest she’d just endured a windstorm. “Pleeease.”

“Okay,” I said. “But promise that in that godforsaken diaper bag you’ll have stashed bagels and cream cheese. And orange juice and champagne. I mean, what if want a mimosa?”

A deal was struck.

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So now I have my Saturday mornings with Jane. Just us gals. Just hanging out. Sometimes we lie around, sometimes we go for a stroll. Regardless, I use our time together to educate her on what the future holds. Specifically, the single gal lifestyle.

I mean, c’mon: Her mommy met her daddy at a ripe twenty-two. Which means that if Jane winds up sailing single through her twenties just like Auntie Sara, well, that business isn’t easy. She’ll need all the help she can get. And I plan to give it to her. And I’m starting the ball rolling now.

With Mother’s day around the corner, I’m reminded that there’s no avuncular Auntie day. So! To all the childless, single-gal babysitters out there — I know I’m not alone! — here’s some of the stuff I think it’s our job to impart.  The list isn’t all-encompassing; it’s simply what Jane and I covered this month.


Ignore The Rules.

Here’s a book that came out eons ago, and still, its ill-founded advice is making the rounds. It’ll encourage you to play hard-to-get, my little one. And while in the short-term you might just procure one or two or five more dates by doing so, I do believe that all the hombres out there for whom you’d have to play hard to get to keep ‘em interested? Let ‘em go. They’re bad news. You’re looking for someone who can handle your neurosis from the get go. Trust me. I know your mom. You will end up neurotic.


Watch out for the old guys.

Inevitably, you will cultivate the attentions of older men. You’ll be nineteen, he’ll be twenty-five. You’ll be twenty-five, he’ll be forty. Now, at the time, you’ll think “Oooo. Look at me! I’m so sophisticated! So mature! I just can’t be with guys my age!” But hear this now: Your involvement with these men will be primarily about the fact that they can’t hang with someone their own age. It’s a red flag of their immaturity, not your maturity. Flirt in your general age bracket.

Related: 18 Guys You Should Never Date


Avoid men obsessed with their bodies.

This is gross and unattractive. You want someone who takes responsibility for his health, of course, but these johns who’re all, like, “Dressing on the side!” “No bun on my bison burger!” “I can’t snuggle you right now; I’m going to the gym!” they are the last thing that you, as a 21st century lady need to deal with. Any delicious bit o’ brawn, you want to make sure it’s somewhat naturally occurring.


Be wary of the unemployed.

To be clear, this is not some feminism slap-down, you- ought-to-date-a-rich-guy thaaaang. Not at all. Be sure you’re financially self-sufficient even if you ignore Point 2 featured above, and wind up Donald Trump’s 37th wife. What I mean is merely that a guy who’s unemployed (and I’m speaking of the gents who are out for work for, say, upwards of a year; I’m talking the professionally unemployed) it’s almost guaranteed to be a lose/lose situation. Because he’s either a) unemployed and bitter, or b) unemployed and happy to stay unemployed. Either way, it’s some dangerous ice to skate on.

As for this week? I’ve already got a lesson lined up on the dangers of men who enjoy discussing their myriad tattoos.

“Sara Barron is the author of People Are Unappealing and the forthcoming Eating While Peeing: and other adventures.