How to Have a Totally Middle-School Romance ... in Your 30s

Exchange playlists of your favorite songs from high school. Interpret it as a sign that they both include The Cranberries and Mazzy Star.
Publish date:
May 25, 2014
relationships, Dating, romance, man child

I’ve always preferred “boyish” to “manly”—big muscles and a strong jaw aren’t really my thing, and I’ll take funny and cute over suave and commanding any day. Unfortunately, it sometimes takes me longer than it probably should to distinguish between “charmingly boyish” and “man-child.” Last summer, I was charmed by a particularly boyish (and slightly younger) dude. Eventually his boyishness became less charming. And then confusing. And then mildly infuriating. After a while I realized I was basically having a middle-school romance ... in my 30s. Sound fun? Here’s how it’s done.

Pass notes.

If you meet online—and you will—email back and forth for weeks before you get together IRL, and keep it up for the remainder of the relationship. Flirting in writing is super-fun and kind of perfect for those of us who haven’t outgrown the tween-ish tongue-tie of a new crush. Plus, he’ll be funny—you’ll be funny together.

Become addicted to the anticipation of each new cleverly titled missive and giddy when it arrives. Be amused when he says he badly wants to like Woody Allen and olives and bleu cheese because they are things that smart, cool people enjoy. Tell each other about art and poetry you like while simultaneously proclaiming yourselves people who aren’t big on art or poetry. When he asks, “Do you like BANDS?” reply, “Yes, but maybe not in all caps. Maybe I’m more into SONGS.”

Exchange playlists of your favorite SONGS from high school.

Interpret it as a sign that they both include The Cranberries and Mazzy Star. Notice how your emails start to sound more and more like his, exuberant and improperly punctuated and flecked with the shorthand of the text generation (obvi, convo, jelly, totes). Think it’s cute when he says things are his “jam” and tells you he’s “stoked.” When he joins independent clauses with a comma, ignore your English teacher inclinations. Instead be all, "He puts together thoughts so creatively!" It’s totes poetic, obvi.

Come to terms with the fact that he’s short.

According to your online profiles, you’re both 5’4". At the craft/junk shop, your agreed-upon first-date destination, find a measuring scale and discover that he’s 2 cm shorter. Afterwards, at a coffee shop, he’ll put his mug next to your slightly taller iced tea. “Look,” he’ll say. “It’s us.” In middle school, lots of guys are short. The question is, can you accept the awkwardness of the height differential? Can you maybe even celebrate it as a physical manifestation of the quintessential awkwardness of the adolescent boy-girl dynamic? Probably you can.

Don’t kiss! Don’t even hold hands! (Just hug a lot, and maybe let him rest his head on your shoulder.)

This issue will arise at the end of a not-so-fun third date at Frankie’s Fun Park, during which you watch him don 3-D glasses and shoot at zombies with a startling lack of self-consciousness and you start to wonder if this boy is a little TOO boyish.

You’ll be sitting in his car outside your apartment when he blurts out, “I really want to kiss you right now, can I kiss you?” Pause awkwardly. Say “Maybe not…right now" because you're flattered, but tired. Think, "Yeah, this is probably not going to work out."

Keep up the email exchange over the next week anyway -- he seems so sincere, so enthusiastic, so into you. When he sends you a link to his Tumblr, be sort of enchanted by the random sequence of Bjork pics and folk-punk tracks, "Breaking Bad" gifs and tongue-in-cheek lists, the super-sweet thing he wrote about listening to Tori Amos with his high school girlfriend.

Start to change your mind.

Invite yourself over for a game of Upwords on his living room floor and feel excited again. Is the ball in your court now? Are you back on the dating track? Unclear. Hang out for a few more weeks in a super ambiguous fashion.Watch a bad 80s action movie on a couch with your legs touching and wish that he would put his arm around you or something. Ideally, "Big Trouble in Little China."

Later, a friend will try to warn you about the maturity level of guys who consider this an appropriate date film. Don’t listen. Have a weird hiatus in the development of your relationship while you both go on family vacations. A full week of lengthy emails and no face-to-face interaction: just endless waves and turkey sandwiches and sandy, restless longing.

Try to figure out if you like each other or LIKE-like each other.

After weeks of ambiguous hangouts and emailing and deciding that you do LIKE-like this guy, revisit the kissing convo. Discover that now HE isn’t sure that he LIKE-likes you—or he does, but he isn’t sure you should date. He doesn’t not want to, but he doesn’t WANT-want to. Something about liking to do vastly different things in your spare time?

Suspect it’s because you said you didn’t want to go on a 3-hour road trip to the nearest IKEA. And OK, maybe you shouldn’t have used the word “anhedonia” when he asked what you like to do for fun.

You won’t be able to pin him down on this. He thinks you’re amazing! He just feels unsure! Feelings are complicated, guys. The logical thing would be to acknowledge that he has a point, however vague. You’re not really compatible. The logical thing would be to walk away. But logic has no place in the evolution of the adolescent romance!

Instead, let the conversation segue into an emotionally charged series of email exchanges and Tumblr posts. Nurse a feeling of heartache totally out of proportion to the situation at hand. Blast old emo songs on Spotify and take long, brooding walks. After a few days, decide to hang out again and try to be all "cool, whatev," when all you want to do is make out. Feel bummed that he doesn’t seem to want to and slightly annoyed that he keeps asking hypothetical questions like, "If you could own a car from the 50s, what car would you pick?"

And then be totes confused when he just stops talking to you.

When you finally decide you don’t want to play it cool, that you want to date, he’ll suggest you get together to talk. And then at the last minute he’ll cancel. And when you email him a few days later, he’ll promise he’s not blowing you off, he’s just very busy working on an iPhone app (!) and it’s all he can think about. And then he’ll abruptly stop responding to all attempts at communication.

Be aghast. Be hurt.

How did you get here again, sporting the adult equivalent of braces and a badly grown out perm, totally insecure and utterly exposed? Resort to the emotional tools of the adolescent: dissect the whole thing ad nauseaum with your friends, pump up the melodramatic pop jams, and write snarky, angst-ridden poetry. Resist the urge to email him those poems, but go ahead and post the hell out of that shit on Tumblr.

And then: move on. Go on dates with guys who seem more or less grown up. These guys may not be as cute or charming or funny or fun—in fact none of these dates will lead to anything—but keep trying. And forgive yourself for the regression. Yes, that inner adolescent gets carried away if you let her, but how bravely she wears her heart on her sleeve.