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A few months back, one of my best friends from high school slept with the guy to whom, years earlier, she had lost her virginity. This time around, though, Suzanne wasn’t 16 and they weren’t in her parents’ basement—instead, they had wild sex in a Las Vegas hotel room. Around the same time, she got it on with the first love of her life, a boy she met during high school, and whom she hadn’t seen since he finished breaking her heart during her sophomore year of college. After reconnecting via Facebook and G-chat, they met up, and eventually hooked up. These two incidents were hardly unique—last year she extensively mined her past for present romantic encounters.

“In 2008,” Suzanne unabashedly shares, “I only had sex with two new people, but I never went longer than nine days without having sex.” There was really only one word to describe her (no, not that one). She had become a retrosexual.

The neology is obvious: Retrosexuals are people who rewind their own lives, digging into their past to emerge with a current romantic partner. So, too, is the cultural context: Like chicken noodle soup or Beverly Hills 90210 DVD compilations, retrosexing lures its participants with promises of familiarity—a comforting concept that’s hard to come by in these complicated times.

A retrosex episode can fall into two major categories, with some subsets: a one-time hook-up or a longer-term romance. The textbook retrosexual, the perfect specimen, if you will, is the former: someone like Suzanne, who hooks up for casual sex with someone he or she knew in high school. Within this group are two narrower classifications: Some retrosexuals, like Suzanne, have been there, done that; others might be reconnecting with old friends but hooking up for the first time.

Here’s an example of a conversation a classic retrosexual might have:

Retro: “I made out with Jon Whateverhisnameis last night!”

Friend: “Jon Whateverhisnameis? That guy you drank vodka with/gave your first blowjob to/studiously ignored at the 11th grade homecoming dance?”

Retro: “Yes! I ran into him/friended him on Facebook/saw his name on a mass e-mail a few weeks ago, and we’ve been chatting—he’s totally great now! We hung out last night and ended up sucking face in an alley.”

Friend: “Weird.”

The other type of retrosexual is someone who romantically reconnects with someone from their past, but not necessarily someone from high school or college. Ex-sex, in other words, but not sordid, desperate, we-just-broke-up-last-week-and-I’m-so-lonely ex-sex. More like, hey-let’s-try-this-again ex-sex. Or, old-habits-die-hard-for-a-reason ex-sex.

Beyond these broad definitions are finer distinctions, such as those who retrosex and then wish they hadn’t (call them “regretrosexuals”), or those who hooked up years ago and have no desire to be reminded of their past romantic encounters (see the sidebar “Fretrosexuals,” by Jeff Inglis).

Typically, the retrosexual must be 25 or older, because true retrosexing calls for some degree of reconnection or rediscovery, not to mention experience. Retrosexing is more common in large cities, where the chances of randomly bumping into an old friend or lover are always higher.

The popularity of social-networking sites—OK, really just Facebook—has made retrosexing all the easier. Whereas potential retros used to have to wait for their five- or 10-year high-school reunions to have old acquaintances fall into their lap, now they can simply search Facebook for high-school classmates and fellow college alumni, and reestablish contact without too much gumshoeing.

Finding each other on Facebook might be how it starts. But how does retrosexualism gain traction, prompting the transition from innocent reunion to romantic attraction?

Consider Gillian and Chad, both 26, who never dated, but were part of the same circle of friends in high school. Their fledgling relationship epitomizes the most common type of retrosexualism: Now that they’re older, they’re reconsidering a previously unexplored romance.

After graduating high school, they ended up at different colleges and lived for several years in different cities. They saw each other occasionally over the years, but neither one ever contemplated romance. Then, about a year ago, both of them ended up in New York City, where they started seeing more of each other in larger groups, gradually planning one-on-one meet-ups. As they became familiar with each other’s adult selves, Gillian and Chad increasingly drew nearer. Recently, they started dating. And while a romance when they were younger would have been unlikely (she was a bit too serious for his class-clown self), Gillian thinks she knows why she went retro.

“As we get older,” she wrote in an e-mail, “it becomes easier to retrosex . . . with old friends, because we’ve more or less finished ‘growing up’ and have less to prove to each other about our lives outside of high school. I also think we’re more likely to be impressed by our high school acquaintances . . . because we’re often surprised by their accomplishments. It’s like, one day you meet somebody, and they’re no longer the dork or loser or loudmouth in high school—they’re a professional man. Which can be intriguing and appealing.”

(The reverse can hold true, too. That guy who was hot 10 years ago might not have held onto his good looks, yet somehow he hasn’t lost his appeal, because you’re “still seeing them through the lens of their high-school appearance and persona,” says another occasional retrosexual, 26-year-old Sarah.)

Regardless, it’s easy to find yourself falling for someone with whom you share a history, whether that history was meaningful (you were involved) or fleeting (you were in the same biology class).

Gillian, who has had two retrosexual encounters over the past few years, describes the strange intimacy of hooking up with someone you knew as a teenager: “There’s a level of familiarity . . . that can actually make things awkward at first. Like, you’re seeing this guy who you’ve gone through so many years with, but now you’re both naked. [It] can be almost comical. . . . But it can also be amazing, because there’s this sense of connection that, although it might not be a true love connection, is unique in that there’s a finite number of people in the world you knew in the high-school context.” (For Chad’s thoughts about all this, keep reading.)

Indeed, that comfort and connection is the whole reason that retrosexing is so appealing, says Massachusetts love expert Paul Falzone, the CEO of the online and in-person dating companies eLove, Together Dating, and The Right One. In these rather desperate times, with the economy particularly terrible for young job-seekers, and the specter of Middle Eastern crisis looming large, all we can be sure of is that we can’t be sure of anything. “Society is going to see more [retrosexing] happening than in the past,” says Falzone. “It’s security, it’s safety, it’s bringing back old feelings that make you feel young again. People are resorting to things they’re familiar with, that they’re comfortable with.”

Of course, that same sense of familiarity is what so often drives us back into the arms of ex-lovers—even more recent ones. Callie, 29, recently reignited an old, extinguished flame after a three-year hiatus. When they met up for beers, after years of relatively sullen, angry silence, she expected a mere friendly reunion. But the outcome was quite different.

“When we saw each other, the chemistry was immediate and intense,” she says. “I remembered both why we were together in the first place and why we’d ended. There was the comfort of the shared past. We had an immediate ease with each other—one that was both relaxed and extremely exciting. A feeling of new romance, with the added benefit of having known each other extremely well. The nervous, fluttery, exceptionally turn-onable [feelings], combined with knowing each other’s backgrounds, likes, dislikes, senses of humors, families, etc.”

It makes sense that retrosexing is so appealing to 20- and 30-somethings, who otherwise feel adrift in their quarter-life malaise: Participants are being permitted to regress. Romancing with people you already know cuts out one of the most harrowing elements of adulthood: forging new personal connections.

“[F]or the first time in your life, you are not automatically surrounded by people your age who are doing the same things you are doing,” wrote Abby Wilner and Catherine Stocker in their 2005 book, The Quarterlifer’s Companion: How To Get on the Right Career Path, Control Your Finances, and Find the Support Network You Need To Thrive (McGraw-Hill). “The challenge of meeting people and making new friends is one of the more common themes in the [quarter-life crisis] community.”

Combine the ease of Facebook socialization with the relative effortlessness that comes with chatting up old acquaintances, and you’ve got the lazy man’s dream-dating scenario.

As with any unique type of relationship, the retrosexual one has its quirks. For one thing, it can be difficult to tell what’s romantic and what’s friendly, especially if the reconnection is made with a platonic premise. After all, archetypal implications of “dating”—like offering to pay for dinner, e-mailing or texting just for fun, or casual physical contact—are the province of friends and lovers both.

“You’re very hesitant to make your move,” says Chad, the 26-year-old who recently started up a retrosexual relationship with Gillian. “You’re afraid you’re going to misinterpret signals. You’re not sure if what’s happening is romantic or not. You don’t know whether you should attempt to kiss the person.”

“The flip side,” he continues, “is when you actually do make some sort of move, you’ll be able to be really bold, because you already have a certain comfort level.” As a result, all those superficial worries—Who will pay? When will she call? Was that brush of the hand a mistake, or was it intentional?—become less nerve-racking.

Another complication can be the inevitable shared-friends group. Not only will the retrosexual duo make waves depending on how, whether, and when they spill the beans about their rendezvous, they’ll also likely grapple with knowledge of their partner’s past intimate experiences. (In fact, this might lull some people into a false sense of security—as though knowing part of someone’s sexual past might make sleeping with them less of a health risk.)

And the better you know someone, the more dangerous it is if something goes wrong. Josh, 28, who sheepishly shares that he’s recently retrosexed with at least three women, acknowledges both the benefits and drawbacks of hooking up with someone you’ve known forever.

“The best part of that is the comfort level you have with someone beforehand,” he says. “Because you know the person, and if the timing’s right, it can be pretty cozy. The danger, though, is that afterward, things can change, and if you’re not careful, you might lose your friend. Which sucks.”

That is exactly what happened to Ellen, a 35-year-old who recently found herself tangled up with an old friend from her junior-high days. When they first bumped into each other downtown, it was amazing, she recalls. They laughed and had a great time. When they finally had sex—once—it was awesome.

But Ellen had recently emerged from a four-and-a-half-year relationship, and wasn’t ready to jump into something new. She told him so. The dude’s extreme negative reaction (we’re talking aggressive e-mails, misogynist talk) was a shock, which made Ellen realize that, while he might be a cool friend, his romantic persona “wasn’t the sweet person I’d thought he was. We simply cannot be friends.” Perhaps if they’d never retroed, they could have preserved their relationship by avoiding romance.

As exciting as it can be, retrosexing isn’t all fun and games. The emotional implications of these blasts from the past can run deeper.

In some cases, retrosexuals seek to achieve something like vindication, or triumph, through their experience. Consider an accomplished, sexy woman who felt significantly less confident in high school—and allowed that lack of self-esteem to color her relationships with guys. These days, if she rekindles an affair with someone who shunned or mistreated her, she revels in having the upper hand. At the very least, she makes sure it’s an even playing field.

“A lot of it is about . . . feeling like I can correct for ‘mistakes’ in the past,” explains Suzanne. “Not just showing off an adult sexuality, but also being able to alter and correct for the power dynamics of years ago. With both S. [the heartbreaker] and J. [the Vegas fling], [her modus operandi] was kind of a, ‘Look at me now’ thing, like somehow, by virtue of seeing them and sleeping with them again and not caring about it, I was reaching back and repairing the hurt that had been done to me in the past.”

She, um, elaborates: “Like, yeah, ‘Look who’s all grown up and hotter than you now, bitches, so why don’t you shut the eff up and eat my pussy for the next three hours. Eff it . . . for the next three days. You’ve got a lot of making up to do for all those bj’s in high school.’ ” (Forgive her, she’s actually a very charming individual.)

And reconnecting with old lovers, ones who you shared time with later in life, can be even more fraught with confusion. Here’s what happened with Callie and her former beau after their brief renaissance: “The insecurities that I linked with being with him, ones I thought I’d gotten over, reemerged. The casual reexploration began to beg the question: ‘What are we doing, are we getting back together?’ which led to hard talks and confusing wants. [A]s we spent more time together, the reasons we’d originally broken up became louder than the reasons we’d been together.”

Still, upon reflection, Anne pinpoints the undeniable appeal of the retrosexual sex-perience.

“I don’t regret the reunion,” she adds. “It was a necessary final chapter. Impossible to resist for the combination of the newness and the familiarity.”

Callie might not be a regretrosexual, but she could have been. Indeed, for every retrosexual fairy-tale ending (They exist! We have Facebook status-change evidence!), there’s a regretrosexual one—which suggests that, even when it comes to love, very rarely can you go home again.

Deirdre Fulton is a staff writer at the Portland Phoenix, where this article first appeared.

Fretrosexuals

Some people really enjoy the potential of reconnecting with folks from the past, and I’m usually one of them. Through the wonder of the Internet, old friends and I have found each other. When I see such a request in my inbox on Facebook, I almost always immediately click “Confirm.” Of course, those reunions haven’t been sexual—just friendly. But the prospect of a reconnection with one person has left me conflicted.

More than a decade ago, my relationship with “Anne” ended. Ours was the longest either of us had been in to date, and we had seriously contemplated our future together (marriage, kids, house, all that stuff). Ultimately, though, it finished badly.

While from time to time I have wondered about what ever happened to her, I’ve never tried to get in touch with her, and she has never contacted me. We have a few friends in common, from whom I have heard ultra-brief updates every few years—“Saw Anne the other weekend” or whatever—and maybe she’s gotten the same about me. But that was the extent of our “contact,” if you can even call it that.

Then last fall, thanks in part to those friends in common, Anne popped up in my “People You May Know” box on Facebook. Of course, I looked at her profile: She’s married, living near Boston, and her photo shows her with a big grin amid a group of friends. All that’s great: Time has healed many of my wounds (though, I find, not all). I don’t wish her ill. I might even have a drink with her if we run into each other somewhere, to catch up. But I’m not proud of how I behaved all those years ago, and I don’t want to revisit those times.

Beyond that, I don’t suffer from the illusion that we have much in common any longer. (Apart from our memories of what happened between us, which are probably more similar than either of us might ever admit.)

Too much time has passed, and what I did in the years since would have happened very differently, if at all, had we stayed together. While I’ve now settled down and gotten married, the person I am today owes more to the fact that things ended with Anne and I got on with my life than to the fact that we ever were together.

So if we did run into each other again, and caught up over lunch or a drink, I wouldn’t expect us to stay in touch, much less to become friends. And I (and our respective spouses) sure would be nothing less than astonished if we wound up in bed together.

Given all that, Facebook is more of a get-in-touch-and-stay-in-touch kind of site. Privacy settings aside, anyone who is a “friend” can see my status and other information as I update it. Distant though it is, I’m not sure if that’s a level of connection I want with Anne.

So I decided not to initiate contact. After about a week went by, I assumed she had seen me in her “PYMK” box and made the same decision. Not so. Another week later, I got a friend request from her: a short, friendly note ending with “It’s been a looooong time . . . “

That was at the end of September. It has now also been “a looooong time” since her friend request, and I still haven’t clicked “Confirm”—or “Ignore.”

But this dallying has only made matters worse. Every time someone sends me a friend request, I have to face Anne, lined up first in the “Friend Request” queue. And all the well-meaning friends I already have on Facebook deluge me with kajillions of pokes, thrown sheep, drinks, and other application requests—never knowing that every time they do, I have to face Anne then, too.

(Almost) every time I see Anne’s request, the debate begins again. If I click “Confirm,” then she’ll be able to see photos, videos, notes from other friends, all kinds of stuff that I’m not sure I want to share with someone who’s not, technically, a “friend.”

On the other hand, if I ignore her request, then I’m putting up the Berlin Wall, severing completely a chunk of my past that, while hanging on only by the barest tendril, was still somehow a connection.

Then again, by virtue of the fact that I’ve taken this long to make any decision at all, Anne probably thinks I’ve long since clicked “Ignore,” and has written me off. The terrible irony is that, as a result of Facebook, I’ve thought about her more—and more often—in these past few months than I had in the last decade.

One last wrinkle: If you’re wondering whether my wife knows about all of this, the answer is yes. She actually brought up the bizarre topic of what do to about old loves in new media because she was wondering if an ex-boyfriend was ever going to show up online. To date, she hasn’t had the pleasure.

—Jeff Inglis

Jeff Inglis is the managing editor of the Portland Phoenix, where this article first appeared.

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