Should You Ever Hook Up with a Virgin

It’s not often a guy has the chance to live out a fantasy as deep and epic as being a woman’s first. Deflowering a virgin is the kind of holy grail that most accept is too grand and too rare for mere mortals like ourselves.

Some pay a fortune to do so, and some save themselves for their wedding night to ensure that parallel, but other than that, taking a girl’s virginity is less likely than being struck by lightning or winning the lottery.

So, when my friend Vince recently found himself in the position of being offered this gift from a girl he met at college, he was giddy with disbelief and excitement and lust.

Should you ever hook up with a virgin, should that rare and impossible dream materialize?

In short, no. No way. Absolutely not. And neither did Vince. Because he, like you, knew that the important thing was thinking about her, not himself.

Here are some of the reasons she is still a virgin, and none of them are ones you want to be entangled with.

She is very young, in which case hands off.

I don’t care about age, from “barely legal” teen dreams to octogenarians. We are sexual throughout our life span and exploring intimate relationships with different age groups is wonderful. But even if she is “old enough” if she is not already sexually active, back off. Let her explore the heat and heartache of sex and love with someone else.

She might be a virgin for cultural or religious reasons.

For whatever reason, she held onto those beliefs and norms, and recently decided to change her convictions. This might be a healthy breaking away from patriarchal cultural tyranny, or it might be wanting to throw something away out of disappointment with God or to embarrass her family or to punish her Dad or to rebel against the rules.

Again, all of this is a woman’s prerogative and part of our growth process, but you can sit this drama out.

She is was waiting for the right guy, for a particular kind of relationship.

If you’re just into casual hookups, you are probably not “the right guy” for her to connect with. Test: are you willing to date her and enjoy her company for six months with no sex before the hookup? Probably not.

She might be really attracted to you and willing to throw all that under the bus—after all, we all get horny, including virgins. But the chances of her hoping for more calls, for connection, and possibly care and love from you after are high, and those are things you aren’t looking for. Don’t take that chance away from her.

She might be emotionally imbalanced.

If a woman is attractive and not religious but is a virgin in her late thirties and doesn’t seem to have a reason, it might be self-loathing, or man hating, it might be any number of reasons for avoiding sex and relationships. In this case, you don’t want to be the one responsible for changing the game. You don’t want to find yourself in hot water, or hang out to dry a needy or unsatisfied lady. Better not to get involved.

There are lots of fun ways to live out the like-a-virgin fantasy—role play and dress-up and reliving your first time or the first time you wish you’d had can be fun hookups with girls who aren’t virgins.

The truth is, unlike Vince, if you’re over twenty and dating online, it’s highly unlikely you’ll ever have to turn a virgin down. But if it does come up, consider yourself flattered, be sweet and kind, and then walk away.