Miss Information

I'm almost thirty and I'm still not over my high school boyfriend. Is something wrong with me?

By Sarah Jaffe

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Dear Miss Information,

My first real relationship was ten years ago, when I was sixteen. I dated my high school boyfriend for three years, and I really thought he was going to be the one. We were a bit on-again-off-again, breaking up finally when we went off to college. I was devastated at the time – he was probably the love of my life. 


From that point through now, I haven't been able to completely shake off my feelings for him. I have dated many dudes, and had one very serious relationship since then, and yet I always wonder "what if...". Recently, my high school boyfriend unexpectedly came to town for an event (he now lives in New York and I'm in LA) that I happened to be attending too. We got together and caught up, and I was overwhelmed by a resurgence of feeling for him. Nothing physical happened, nor did any deep convos occur due to time being against us (he was in town for just a day), but it definitely threw me for a loop. It seemed as if he may have had similar feelings, but it was hard to tell and it never came up.

I'm a very grounded person, and my rational brain says that it's crazy to still be feeling these feelings for someone who I dated so long ago and who seems settled on a completely different coast. My gut feeling is that I shouldn't be suppressing this reaction, but rather acting on it to get closure one way or the other, since it feels strange that these feelings are STILL affecting me while with other, much more recent relationships I was able to fully move on. Do I pull the romantic comedy move, and contact him to tell him how I'm feeling? 

—Ancient History Revisited

Dear Ancient History,

Ah, the classic rom-com move! Dramatically confessing your feelings to someone who may or may not be completely inappropriate is always good news if it comes at the end of a movie (in which case, the audience can expect wedding bells, or a horseback ride off into the sunset, or at the very least a passionate kiss with triumphant music swelling in the background), and terrible news when it comes at the beginning of the movie – that means we’re in store for a poignant, laugh-filled romp to rock bottom followed by eventual redemption. So the question is, are you at the beginning or the end of your movie?

My general rule for telling people how you feel is to just freakin’ tell them, unless telling them will seriously fuck up your shit (i.e., you’re in love with your boss or your cousin or your best friend’s significant other, in which case keep your lips zipped, dummy). It sounds like telling your ex you’ve still got a little candle with his name on it burning in your window will cause exactly zero fuck-uppery of your shit – you live on opposite coasts and you’ve had minimal contact over the past few years. The worst that can happen is that he’s absolutely not interested, in which case you dust yourself off, remember your first real relationship fondly, and finally move on to find someone new who’s never made out with you in your parents’ basement (yet?!). There’s no friendship ruined, no potential for awkward accidental run-ins, and best of all, no ambiguity left for you to wonder about. There’s nothing for you to lose here beside a fantasy you like to fall back on when you’re feeling crappy about your love life. Sounds like a pretty sweet deal. 

So let’s say you pull a rom-com and it turns out he’s never really gotten over you either: you’ve got the awkwardness of a bicoastal long distance relationship. Which doesn’t sound ideal, but hey, if the tiny voice in your head muttering “what if what if what if???”  is right and you guys are soul mates after all, you’ll figure it out. Or you’ll try things out and realize you were maybe just nostalgic for the intensity and magic of a first love and that reuniting with your ex isn’t as amazing as you’d dreamed it might be, but no matter how it shakes out, you’ll know for sure. If there’s one thing we know about rom-coms, it’s that they’ve got very neatly buttoned endings. Go forth, dear ingénue! We’ll all be over here eating popcorn and rooting for you. 

Image via Flickr.