My buddy is an actual 40 year old virgin. Should he tell this to a woman if he ever goes on a date?

I think not. It may qualify as one of those ‘only on a need to know basis’ tidbits of information. He should at least wait until he in the process of slipping it in. If she freaks out, TOO LATE!

Aside from that, the movie might have some pointers. I hated it, but I also wasn’t watching it from an instructional video point of view.

NO… first of all, what she doesn’t know wont hurt her, and second, it would seem as if he is going out for sex only ( even if he is, she should not know)
Just tell him to go and enjoy and maybe he’ll get lucky… eitherways, good luck

First of all, it’s nothing to be ashamed of, and I think most women would be sympathetic and not overly judgmental. However, one’s virginity is too heavy a topic for early dating and potentially sends the wrong message. It’s one of those things that should eventually be told, but not until later, when the foundation is laid, i.e. after several dates when it seems like the woman is into him and the relationship and when there’s a definite possibility of becoming intimate.

It’s like the question a few days ago, where even before the first date, a guy warned the girl that he had baggage. Having baggage isn’t necessarily a bad thing, but saying so before even going out puts too much emphasis on the issue. Things like this need context, by which I mean the other person should first have some idea of one’s personality, them being a good person, etc. Bringing it up too early could be disastrous and puts way too much emphasis on the issue.

It’s far better to wait, get to know the woman and vice versa, and then in a moment of intimacy, bring it up. So, like, if they’re making out and it looks like it may progress further, he could say, “So, this is kind of embarrassing, but I really like you and I have to tell you something.”