How to Date Your Old High School Crush (and Why You Should)

How to Date Your Old High School Crush (and Why You Should)
Photo: Rido, Shutterstock

Dating in high school is hard. You’ve got wild hormones, an overwhelming curiosity (paired with trepidation) about sex, loads of pimples, and a shaky sense of self, the world, and where you fit in it. During this time of shape-shifting self-esteem, it’s easy to think that the people you had epic crushes on — the ones whose hands you’d longingly watch scribble biology notes, whose yearbook pictures you’d memorise and lockers you’d casually stalk — were way out of your league.

Fast forward 15-20 years (give or take). Dating is still hard, but you’ve realised: Hey, I’m actually a catch. You’re no longer that unsure teenager of little life experience and questionable confidence. You are a whole, fully-formed adult, who has had jobs, degrees, travels, career achievements, perhaps even marriages or children. And during the intervening years since high school, you’ve learned that what you have to offer another person is pretty great, and you just might be able to land that person you thought was so unattainable when you were 16.

Now, if you’re happy with your current dating life, carry on. (Ditto if you recently graduated high school and haven’t gained the requisite time, distance, and experience outside of your hometown to make going back to it a form of poetic justice.) But, if you’ve given yourself a chance to sample the universe of eligible singletons in the “the real world” (and found them lacking), it may be the right moment to turn back the hands of time and see what your old crush is up to.

Why you should date your high school crush

Have you ever tried online, speed, or blind dating? If so, you may have noticed, it sucks. Sifting through stranger upon stranger to land on someone who is not only sane, but also intelligent, trustworthy, loyal, and shares your lifestyle, morals, and values is a lot of work. People have lost weeks, months, and years of their lives to this pursuit. (Not to mention the sheer emotional damage.) Here’s why it’s beneficial to revisit the hottie from your AP English class.

They’re vetted. There’s no substitute for the depth of knowledge you have on a high school crush. You already know so much about them — where and how they grew up, the friends they choose, how they treat people, their outside interests, who they’ve dated (and sometimes, how they treated their ex after a breakup). You may even know their parents, siblings, and if you grew up together, what they were like in kindergarten. Private detectives couldn’t give you this level of intel on your latest Tinder match.

You have shared history. Whether you had a platonic friendship, a charged flirtation, or barely spoke to each other in band, the fact remains: You have things in common. You had the same teachers, went to the same football games, walked the same halls. While it can be limiting to stick with this familiarity right out of high school, after some years away, it can be wonderful to reconnect with. (And even if it only lasts one date, you’ll have plenty to talk about.)

Mutual connections. Knowing many of the same people has its advantages. You know not only the type of friends they keep, but it facilitates conversation, promotes a bonded feeling, and can make group social interactions easier.

How to date a high school crush

Finding an old flame from high school requires nothing more than social media and rudimentary Googling skills. But once you’ve done the requisite friending/following, liking, commenting, and direct messaging, here are a few things to keep in mind when you actually reconnect IRL.

Manage your expectations. You may meet and find that your crush was not as amazing of a person as you thought, and they have some issues. Maybe life’s been hard and they’re still a good person, but not a good person to be in a relationship with. You may find that how they look or act decades later is a turn off, and you’re no longer attracted to who they’ve become. Or you may still think they’re great, but the chemistry isn’t there.

Know that it may bring up old insecurities. One of the great things about dating new people is that you can be your “new” self — the one who has grown and matured by leaps and bounds since your teenage years. Sometimes, reconnecting with a person who intimidated you when you were 17 can thrust you right back into that insecure emotional world. Remember they’re just feelings, and they don’t erase all you’ve accomplished since then.

Recognise you may be more into the idea of dating them than the reality. Your life circumstances, values, senses of humour, or lifestyles may be too far apart to make a love match. And that’s OK. Now you can close out those lingering feelings once and for all, with a sense of worthiness and pride in how far you’ve come, and no more pesky “what ifs” burning a hole in the back of your mind.

Embrace the possibilities. Of course, it’s entirely possible that the person you mooned over in high school is as amazing as you thought; all you needed was the right time to come along for you to reconnect. And whether you enjoy a short or long time together, you can go forth satisfied with your courage to rekindle things, and secure in the knowledge that you were right all along.

  

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