It Happened To Me: I Ended Up In Bed With A 27-Year-Old Virgin

He waited until he was putting on a condom to inform me that he’d “never done this before.”
Publish date:
April 24, 2013
Dating, virginity, condom, M, Sex,

Here’s the thing: For the last few months, I've been on kind of a dating kick. But it ended recently because, well, shit got kind of real when a man I was thisclose to sleeping with told me (read: sputtered at me), "I've never done this before."

Good lord.

This is how it went:

After amicably (although profoundly sadly) ending my relationship with a man I loved very deeply, I had

to get my sea legs, so to speak. But really what I ended up getting was my sea drunkness. And my sea promiscuity.

Because damnit, I'm a confident 20something with a grown-ass job and it's Wednesday and I'm alive or whatever that quote from "Girls" is.

Anyway, I jumped into the seventh circle of Hell that is OKCupid and went on a bunch of dates. It was pretty easy to do -- I’m gainfully employed and live in a city where, statistically, women have the upper hand in the dating pool -- and I basically started kind of collecting men like Pokemon.

I'm not proud. OK, I'm a little proud.

In the midst of this Katamari ball of mostly-forgettable, frequently problematic men, I met one who was shy and sweet and seemingly well-adjusted. He had a real job and a real place to live and wasn't sketchy and didn't really seem into bullshitting around. He was cute and stylish and we had enough things to talk about, so I was hopeful that, while I wasn’t looking for a relationship, the idea of going out with someone kind and not-weird for a while sounded pretty appealing.

And he followed up with polite texts and liked to make plans, so we did go out a few times. Three times, to be exact.

Which, interestingly enough, is the exact number of times it usually takes to go from “Should we sleep together?” to “Yeah, might as well just sleep together.”

That wasn’t how it went at all, though. Oh Jesus Christ, it wasn’t. And not for any reason I was even mildly prepared for. Because I don't know if, after a sex bender, you can ever prepare to feel the feelings you feel when the man with whom you're between the sheets tells you he's never had sex. Never. Had. Sex.

Maybe I should’ve known by his relative clumsiness at everything leading up to sex, but then, a lot of guys in their 20s are still pretty fumbly in that realm. But honestly, there were no firm clues.

It’s not that surprising -- with teen sex rates going down, there must be more 20-something virgins walking the earth, right? But to be fair, the vast majority of Millennials have already given it up; by age 19, seven out of 10 women have already had their first sexual encounter.

To answer all of your questions: No, he wasn’t religious. No, he wasn’t bad-looking. No, he didn’t appear to have anything critically/criminally/pathologically wrong with him. He was just very shy and very smart, and I think the combination successfully cockblocked him throughout college and well into a smart-person job that has almost no dating prospects.

I’m fairly sure that the reason I was so shocked was because he didn’t tell me during our walk back to his place, or during that awkward time when we were on his couch looking at each other with very little left to say. (Turns out, it was so awkward because he legitimately didn’t know how that situation usually pans out). Or even when it became clear that sex was imminent and I started unbuttoning my dress.

In fact, he waited until he was putting on a condom to inform me that he’d “never done this before.”

After the shock, there were two options, really: Do it with the awareness it would not be good for me and potentially emotionally difficult for him, or don’t do it and leave the poor dude still standing with his V card firmly in his trembling hand. So naturally, I went into caring stranger mode.

“Oh, jeez,” I stammered. “OK, we need to stop.”

Internally, I was screaming at myself to not laugh, not make a face, not judge. He definitely didn’t need that -- and really, he should get points for honesty, right? But outwardly, I was ultra-calm.

“I don’t think I can be the person you do this with. I’m not going to be your girlfriend, this isn’t going to be a relationship -- and you probably should do this with someone who is,” I told him as placidly as possible. He just groaned.

For a split-second, I did consider another possible plan: Come back at a later date for the mercyfuck. Maybe he just really wanted to get it over with, and I could be the somewhat-slutty (in the most positive way) lady who could come along and help him get over the hump of virginity. But almost immediately, I realized what a terrible idea that would be, because this did not seem like the kind of guy who could go from zero to 60 and suddenly start having casual sex.

In the end, I had to just leave his apartment and know that there was a very good chance I wouldn’t see this man again. It was just too sticky of a situation, and one that felt more appropriate for someone else to handle. Maybe if I were a kinder person, I’d have been more willing to assist -- or maybe it’s a super-entitled, narcissistic thing to assume that he’d even really wanted me to.

He waited a full week to text again, and when he did, he asked me to come over and watch movies, which, with any other guy, I’d assume was code for “have sex with a movie playing somewhat uncomfortably in the background.” But with a virgin, it was all new territory.

I didn’t respond, which I don’t think was the right thing to do, though, in this story, I don’t know that there was a good outcome possible. Maybe there was -- I’m sure you’ll tell me what I should have done.