On Losing Your Virginity (And Your Regret)

Maybe the first time you had sex, it was with your long-term significant other; maybe it was with someone you’d just met. Maybe you were 16 and it was…alright; maybe you were 23 and it was fucking incredible. Maybe you were too sober; maybe you were appropriately buzzed. Maybe you lost it to a girl; maybe you lost it to a guy. However you did (or will do) it—on a bed, in a trunk, upside-down, sideways, fast, slow—your first time probably was (or will be) a brew of mild discomfort, heightened self-consciousness, and relative pleasure.

According to Glamour, about 90% of us regret our choice in partner the first time we have sex. At the risk of sounding like an inspirational Hallmark card, I take issue with the term “regret” in this context. Because if the sex was consensual, there was a point when you thought it was a stellar idea to lose your virginity to that person. And whether you did it with someone you now love or now hate, your first time was likely short of outrageous.

So why bother with regret?

I would venture that the only people who characterize their first time as amazing (or wretched, for that matter) are those who view virginity as some sort of sublime gift/prize/treasure/accolade. Because if you consider losing your v-card a big deal, your big expectations are either going to be met (yay!), or trampled upon (boohoo!). Personally, I don’t think anyone should subscribe to bullshit ideas—whether purported by parents, friends, or gray-haired preacher dudes—regarding when and how (or to whom) you should lose your virginity. I have a progressive attitude towards sex, I guess, probably by virtue of being raised by particularly liberal parents in New York City, where young people generally speak in an unreserved sexual tongue. So, largely as consequence of my upbringing, I just don’t think there’s one great or even good way to do it. To be honest, I just don’t think losing your virginity is all it’s cracked up to be.

So for all you “regretful” of that first person with whom you did the dirty deed, I have a gentle directive: Don’t be.

Do you remember Oliver? Oliver is my dear friend I mentioned a few weeks ago—the one woefully entangled with Harry. In that post, I mentioned Dylan, Oliver’s “maniacal ex.” Anyway, Dylan—yes, deranged Dylan who referred to Oliver as his “little brother”—was Oliver’s first.

When he got to college, Oliver hadn’t had many same-sex sexual experiences; he’d gotten with plenty of girls in his life, but since coming out, he hadn’t had many opportunities to get with dudes. So when a hot senior seemed intensely interested in him, Oliver was receptive. A month or so into the relationship, Oliver (not so subtly) began hinting that he was ready to have sex.

For almost two weeks, Dylan hyperbolized the hypothetical experience.

“Are you sure you want to do this?” Dylan would ask. “Are you definitely ready? I just want to make sure you know what you’re getting into.” He continued to ramp up the theatrical quotient: “I need you to be positive that this is what you want.” And finally, the ever-nauseating, “I’m just…not as good of a guy as you think I am.”

It was his virginity, for Christ’s sake, not his impending deployment to ‘Nam. At this point, Oliver was so frustrated by what had become the Lifetime original film, Does Oliver Really Want To Bone?, he almost wished he’d never suggested it. But since the closing credits were upon him, Oliver saw no point in changing the channel.

The sex wasn’t great. But it wasn’t bad, either—a little uncomfortable (physically and otherwise), but no more so than expected. What was unbearable was the pillow talk. Immediately after they’d finished, Dylan posed the most enigmatic question he’d asked to date: “So…do you consider yourself deflowered now?”

Doing his best to keep his cool, Oliver riposted, “Uh… yeah…?”

Unsurprisingly, the two soon parted, leaving Oliver mortified by what he viewed as a blemish on his sexual history. That is, until he had enjoyable sex with a totally normal guy.

See, that’s the thing about the person who “takes” your virginity: Once you’ve moved on from the (maybe cringe-worthy) individual, you don’t give a shit about them anymore. If you do continue to give a shit, it’s because you view sex as more special/memorable/newsworthy than it really is. Novelty will do that. But novelty inevitably fades.

Most of us have had/will have a regrettable sexual encounter (or four) somewhere along the line, so we might as well drop the tendency to regret that first time. In reality, it ain’t any more important than the second, third, or fourth.

Regret weighs a shit ton, so why lug it around unless you absolutely have to?