How Soon Should I Tell A Date That I’m a Virgin?

Dear Evan,

I am 27 and a virgin. I am sure that no one expects this of me 🙂 How do I address this issue when I meet someone “quality”?   As a man, would you expect to learn what you’re “dealing with” or would you rather not be freaked out in advance and learn it in the process? 🙂 Thanks!

Milisenta

I’m nineteen years old, I know there is a problem with me because I can’t seem to have a long-term relationship with a guy. The longest of my relationships lasted about three months. I’ve dated a lot, since I never find what I’m looking for, and I always end up giving up on them or if I get rejected I feel like I’m not good enough. It seems like all the “normal” guys are already taken. And I don’t know what is it that I’m doing wrong. Also, I think I’m always attracted to the same type of men (jerks).

Another thing that concerns me is that I’m a virgin, and I like older guys, so it is a bit of a problem, and I won’t get physical with a guy even if I like him a lot because I’d like to get to know that person better before sleeping with him. Nowadays it is like if guys don’t get that, they will walk away from you. I know sex is super important in order for a relationship to work out, just as chemistry is, but if I don’t get to know him first, how am I supposed to feel comfortable to do it?

Now whenever I meet someone new, as soon as I can, I’ll let him know I’m a virgin. Do you think that’s bad?? Should I wait to know them better before telling them?

Please let me know what you think!

Hely

I’ve printed these two letters back to back because…

-They’re letters from two virgins. (Yay, virgins!)

-They contain some universal themes that our older readers can definitely apply to themselves. And yes, everyone reading this is probably older than 19.

First, let’s look closer at Hely’s question:

I’ve dated a lot, since I never find what I’m looking for, and I always end up giving up on them or if I get rejected I feel like I’m not good enough. It seems like all the “normal” guys are already taken. And I don’t know what is it that I’m doing wrong. Also, I think I’m always attracted to the same type of men (jerks).

This letter did NOT have to be written by a 19-year-old. I think many of us can relate to her issues today. And I, for one, want to protect her from writing this same email to me in another twenty years.

So, in brief, I will tell you this:

If a guy isn’t treating you the way you want to be treated, leave him. It’s not your job to change him.

If a guy says he cares about you, but doesn’t back it up with his actions, leave him. It’s not your job to change him.

If a guy wants you to change for him in a fundamental way that is uncomfortable to you, leave him. It’s not his job to change you.

Which brings us to the meat of your question: should you tell him right up front that you’re a virgin?

Actually, no. I don’t think so.

But to explain my position, let me share with you the two virgin stories I have in my massive portfolio of dating tales. … This is NOT the story of how I lost my virginity (It was to a stranger from EastCarolinaUniversity), but rather, two stories of how I confronted two women who told me they were virgins early on.

One of them was back in college. We dated for a few weeks. She asked me to take her virginity. I knew I didn’t see myself with her long-term so I broke up with her. Better for her to find a guy who cared about her than to be with a guy who slept with her and left her shortly thereafter.

The next time, I was probably 30. My date was 27. She confessed to me before we ever went out that she was a virgin. She didn’t feel that she had to be married first, but wanted, at least, to be in love. I respected her honesty and thought she was very cool. We went out a couple of times and never slept together, which was probably for the best.

So what can we learn from these stories of innocence and sexlessness?

Well, for one, we learn that it can be extremely easy to take advantage of a virgin. All I had to do is act like I cared for a couple more dates and I could have de-virginized two women. It sounds awful, but there are some guys who think this is hot, the highest notch you can get on your bedpost. Sex with a virgin is next to impossible once you’re in your twenties. And who doesn’t crave an appointment with the impossible?

The problem, Hely and Milisenta, is that you can never tell which guys REALLY care about you and which ones just want to be able to say they slept with a virgin.

Which is why I’d advise you to keep your mouth shut. Yes, there are men who might be turned off by your lack of experience. But there are also men who might be turned on by it.

The best way I see you dealing with this issue is not to make it an issue at all. Go out with men, let them chase you, let them flirt with you, let them kiss you, let them touch you. You can probably go out on a good three or four dates before you actually have to have the “sex” conversation.

And at that time, just be honest. Mostly.

“I didn’t want to freak you out or make a big deal out of this, but I only want to have sex with someone that I’m in a committed relationship with. I’m really attracted to you, but until I’m sure that we’re going to be boyfriend/girlfriend, I have to keep saying no. How do you feel about that?”

From here, you can gauge if he’s serious about YOU or about SEX, and you don’t even have to “out” yourself as a virgin. If he makes it clear that he wants to be in a relationship with you, you can decide if you like him and trust him enough to be your “first”. And if so, THEN you can tell him that you’ve never had sex before.

And if I’m reading this wrong — if you NEVER plan to have sex outside marriage — this is something that can be brought up once the conversation arises organically. The same way that I might really want to have kids, but won’t start discussing baby names on the first date.

Good luck finding a guy who makes that first time worthwhile!