Ask Him: I'm Dating a Virgin

The dude I am dating is a virgin. Not religious, but a virgin, and I don’t know what to do.

dangling that carrot.

dangling that carrot.

Wait a second. I should cover my ass immediately on this, before we get started with the whole me-telling-you-what-I-believe-you-should-do-about-this-issue thing.

I have no idea who you are or, more importantly, how old you are. So I will address you as a 26-year-old.

(If you are a 14-year-old or something, then what you should do is go to the movies with the dude you’re dating and, I don’t know, make out. Maybe indulge in a little under-the-shirt-over-the-bra action. If he tries the “hole in the popcorn bucket” trick, take a picture with your phone and then blackmail him. WHATEVER YOU DO, DO NOT MAKE HASTE TO TAKE HIS V-CARD.)

Next, I’m prone to say, congrats. This may seem like a weird thing to be congratulated for, because it totally is; you have landed yourself in a supremely weird scenario, lady. These days, dating somebody our age who is a virgin for non-religious reasons is a pretty significant rarity. You’re presented with the opportunity to be not only the first person your boy sleeps with—but without getting too ahead of ourselves here—THE LAST.

What should you do? Talk with him about it. Maybe you have already done this. I assume it’s how you came to find out that he is a virgin. (Bet it feels weird to be the one who gets turned down while getting fresh, doesn’t it?) If this is the case, I apologize for patronizing you, but talk about it with him some more. If a guy goes this long without throwing away the V-Card, there is a reason for it.

Once the reason has been breached, make him feel comfortable discussing it. (Unless, of course, it is a really crazy reason, which I am ruling out based on your assertion that his abstinence is not encouraged by Jesus Christ or L. Ron Hubbard.) If he has gone this long without having sex, it’s unlikely he’s just going to lose control of his faculties and let one “randomly” slip in without some serious dialogue and internal debate.

At a certain point in the conversation and your subsequent solo debrief(s), you should be able to decide if you want to stick around in an effort to be his first, and if you do, how long you may have to wait to complete that mission. And how long you are willing to wait.

If you’re going to throw in the towel, let him know. He can’t be mad that his decision to not make with the banging is something that would eventually drive a potential suitor to more experienced pastures.

BUT. If you’re going to try to get him to exchange his virginity for the greatest feeling in the history of anything (for real, I’ve tried it), then the only advice I have for you is: really go for it.

What I mean is, keep wearing him down. Motivate yourself with the knowledge that if you succeed, you will not only get your rocks off (eventually, it may take a few rounds since he is a beginner, unless you get him real drunk!), but you will also be introducing a human being to SEX. There is no greater gift, really.

Take it step by step. Base by base, as it is. Ensure that you approach the deed with a certain amount of pageantry. The longer you wait to have sex (if it’s by choice), the less willing you are to give away the milk for free to somebody who has been indiscriminately consuming calcium for the past decade or so. Get to know his body and his sexual insecurities. Encourage and allow him to do the same re: your body and your practiced sexual preferences. I am confident that, using this approach, you will eventually reach a point where he can slide into home and the two of you can have a hell of a lot of fun doing the sex thing.

If and when you seal the deal, bring your A-Game. You can be this guy’s Gold Standard.

Also, print and laminate a V-Card that you keep in your purse. You know, make it tangible.

I wish you the best of luck in getting laid. Please email me a digital high-five if and when you do, whoever you are.

All the best,


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