Bed, Bitch & Beyond: A Hook-Up Deferred--Shameless Tales of Reconnecting with High School Crushes

Yesterday I was browsing the magazines at my local newsstand and came across a Time magazine article entitled “Facebook gives birth to the retrosexual”, a not particularly alluring term for what happens when you meet up with a crush from your past–not ex sex so much as a second chance to hook up with that hot girl or guy you missed out on in high school. The article claims that: Most retrosexual experiences seem to spring from an intense, almost uncontrollable mixture of nostalgia and interest.

The Time article follows a couple stories of “retrosexual” encounters (the last time I’m going to use that word, I think). My favorite was that of 30-year-old Jillian Stein, who reencountered three of her high school flames, with mixed success:

She reconnected with her first crush, “the embarrassing kind where I couldn’t even talk to him, I liked him so much.” He had liked her too; they confessed their old crushes on each other through MySpace and arranged to meet in person the next time Stein was in town. But when she met him at a bar, she was immediately disappointed. He had gained weight, worked in a dead-end job and had already been engaged three times. “I was like, um, no,” she says.

The third meeting — with a boy whom Stein would occasionally meet after high school for what she describes as a “behind-the-bleachers sort of thing” — went differently. He found Stein on Facebook, and they began talking. Stein added him to her list of people to see. They met for dinner, but “it was beyond awkward,” and their conversation felt forced. So they left and went to a pool hall.

Several hours and drinks later, the former flings were kissing. Then Stein went home with him. In the morning, she made the drive of shame back home to her parents’ house. “Here I was, almost 30, and my mom was so pissed at me,” Stein says. She felt as if she were back in high school.

Stein doesn’t know what inspired her to do something like that. They knew each other. They had talked extensively through Facebook, and their fling felt like more than a one-night stand. But it was definitely less than a real relationship. They had a history, a rapport. They weren’t just hooking up; they were doing something they had always wanted to do but had been too young to try. “It was fun,” says Stein. “I got this really great closure, and it felt safe in a weird way.”

Social networking’s latest contribution to society: realizing the drunken hook-up deferred! I confess, had a very similar experience a few years back. In high school, I’d had a huge crush on a boy in my older sister’s class, who I’ll call Jake Ryan. He was smart, he was funny, he was on the crew team…I seriously had the hots for him. The last time I saw Jake was at a U2 concert just after graduation, when I bumped into him and some other high school friends at RFK Stadium. About 10 years went by–I moved to New York, he went to law school and then moved back to our hometown and bought a house not far from our high school. And then through the magic of the internets, he found me. When he was in New York, he called me and asked me to have dinner with him. The “almost uncontrollable mixture of nostalgia and interest ” hit me hard. I pulled my hottest date outfit from of the closet–it involved black leather pants, as I recall–and headed downtown to meet him.

Jake and I had a great time catching up, and after a couple gin and tonics, I confessed my past crush. He seemed flattered and we breezed right past that revelation and onto other things. But a few hours later, we found ourselves on the Brooklyn Bridge, gazing out over the harbor, and Jake turned to me and said, “You know, I wish I’d known about that crush back in high school.” Furious making out ensued.

The rational 27-year-old part of me was thinking logically: “Wow, this is so weird. Who knew?” but was almost instantly overridden by my inner 17-year-old, who was jumping up and down, squealing “OMIGOD OMIGOD OMIGOD, YOU’RE KISSING JAKE RYAN!”

When I got home that night–even though it was past midnight–I immediately called my best friend from high school and as soon as she picked up the phone blurted out, “Oh my God, I had dinner with Jake and we totally made out.” There was a long pause on the other end of the line and she said, “Jake Ryan? Seriously? From AP History?”

On my next trip home, I saw Jake again. One thing led to another and…I got to have sex with my high school crush. And I’m sorry to report, gentle readers, that it was only so-so. The heated teenage fantasies had been way better than the tepid adult reality. And to make it even worse, after I left in the next morning, he didn’t call me again for six months.

Had he been any other ho-hum one-night stand, I probably wouldn’t have cared. But this was Jake! We had shared history! How could he behave like any other 20-something guy? Any hope of belatedly finding true love with my high school crush belly-flopped with a resounding splat.

Jake Ryan did eventually resurface, and apologize. Aaaand…I may have had sex with him again just to see if it would improve on the second try. (It didn’t.) But I have no regrets. As Jillian Stein said in the Time article, it was fun, safe, and gave me a weird sense of closure. Jake Ryan and I went back to being friends, and–oddly enough–he’s now in a serious relationship with another girl who we went to high school with.

One of the stranger realizations I’ve had about getting older is that there’s real pleasure–both emotional and, potentially, physical–to be had in reconnecting with people from an earlier phase in your life…even people you never thought you’d see again (or even people you never wanted to see again). In past centuries, people rarely moved far from where they were raised, and generally maintained the same social network for their entire lives. In our modern society, we’re highly mobile, but social networking sites give us the chance to rebuild the connections that we thought we’d lost, sometimes in unusually rewarding ways…

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3 Comments Have Been Posted

I can almost 100% relate to

I can almost 100% relate to this.

A couple of years back, when Facebook first started and was only open to college students, I joined, and went looking for some of my old high school friends. Out of curiosity I typed in the name of my old crush, and wham! There he was. He was a grade ahead of me, smart, really cute, and somehow I met him through a friend and we engaged in a mild flirtation for the pretty much the whole year, and then i asked him if he wanted to hang out sometime.... and he said he'd let me know. Sigh. but I still had a mild crush on him, and when he graduated and I saw him at the homecoming game I went right up to him and started chatting away, still having a crush on him but it never went anywhere. Flash forward like three years, and I found him on facebook, and I have a boyfriend, but those feelings were still kinda there. So I added him and he remembered me and we talked on AIM and FB and I really thought of breaking it off with my boyfriend and try it with him. I thought about meeting up with him during christmas or spring break, but I just couldn't. I liked my boyfriend too much, and didn't want to risk being rejected and then be alone and without the man I really did like. So we eventually stopped talking.

Then I saw him. I was working as a barrista in a corporate office building and he was doing some sort of training at the nearby hotel. I froze. And it freaked me out. I really thought about running to the back because I started shaking and I pulled myself together and we shared a few words, but after seeing him, after all those years, I realized I was more into the image of him and not really him. Unfortunately as I kind of got to know him through talking on AIM he seemed nice but a little devoid of personality. And I am really glad I didn't break things off with my boyfriend because we just got engaged last month.

I think it's really neat that Time decided to write an article about this because the wonders of the internet are truly amazing. And it is a bit risky to seek out that old high school crush because you have this image of this other person, and then years later when you reconnect, it can be very disappointing if they don't live up to your image of them, at no one's fault. I totally had an image of my old crush and he was nothing like it (he reminded me of a 50s greaser but he was anything but).

This is a great article.

This is a great article. This July I reconnected with an old flame from high school. After 4 weeks together he clearly couldn't maintain the act he was putting on for me and his friends. He hadn't changed at all, still the selfish, arrogant a**hole I remembered. You would think (I hoped) that he wold have matured past high school.

Note to self: NEVER go backward!

" No matter how love-sick a woman is, she shouldn't take the first pill that comes along." Joyce Brothers

What if..

you're "reconnecting" with people you never lost touch with?

I'm still in college and it seems like every time I go home for a break, some new couple/friends-with-benefits situation has arisen among my close-knit high school friend-group. There even seems to be an "I'm in a relationship but it doesn't count" clause.

Full disclosure: I made out with a high school friend myself a few months ago, and got that same "safe" feeling. (Also had a great time!)

Are my friends so nostalgia-obsessed that we can't even wait until we graduate to rekindle "old" flames? Or is this a separate phenomenon?

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