Intimate Inquiries

I am interested in starting a romantic relationship with one of my close guy friends, but there is a problem. He is a virgin and I have slept with more than 10 men. I don’t want him to think I’m a whore and I want him to take me and our possible relationship seriously. He has told me that he is interested in starting a relationship, but he shows signs of hesitation because of what he knows about my past. What should I do to make him more comfortable with the idea of us being together?

Promiscuous Girl

Dear PG,

Just because you’ve got some R-rated experience doesn’t mean you can’t bag a goody two-shoes. In the early stages of a relationship, your sexual history really isn’t any of his business so don’t feel like you need to explain anything to him at this point. If he’s already heard it through the grape vine, he’s likely just intimidated by your veteran status.

If you want him to take the potential relationship seriously, you need to first ask yourself if you’re doing just that. Since this guy is your friend, the most important thing is ensuring that you’re not taking this potential relationship lightly. While it might seem like it’s a given, there are a lot of not-so-right reasons that might cause you to think you want to start up a relationship with your friend. The fact that he’s a virgin, a close friend and a potential challenge are some that come to mind. If you’re certain your motivations are altruistic, then you’ve got the green light from me.

The best thing you can do is take things slow, be as straightforward as possible and make yourself aware of his potential concerns. His anxiety either lies in the thought that he might not live up to your expectations, or in the idea that he might take striking up a relationship much more seriously than you do.

First, make sure to scale back the seduction factor. His lack of experience suggests he’s probably not as comfortable with aggressive women as you might be with aggressive men. Let him know you’re interested, that you’re aware of his concerns and that you’re sincere about the prospect of a relationship — then be ready to sit back and wait for him to come around. Don’t go looking for love elsewhere in the meantime, and don’t pressure him into anything physical early on.

If you really like this guy and you’re truly concerned about his comfort level, you’re going to have to take things slow and prove to him that he won’t just be the 11th notch on your belt.

I have a friend who has never spent a single second in a classroom, never driven a car or ever had a job. He is 23. He manages to live a full life by taking advantage of this sweet girl that loves him, drives him everywhere and pays for everything. He doesn’t love her back but feels that if she is willing to drive him everywhere then that’s her prerogative.

I feel like the girl is only doing things for him in hopes that he will develop feelings for her. He says that there’s no chance of that happening. I’m trying to show him that he needs to take care of himself and stop depending on this girl or she’ll get her own life and he won’t be able to do anything.

I want to convince him that the good times won’t last forever and that he should man up and depend on himself. Am I wrong to try to meddle?

Mister Meddler


Short answer: Yes.

Long answer: In the off-chance that he ever even ASKS for your advice, you MIGHT have the opportunity to convince him to change his ways. If this once-in-a-lifetime chance comes up, let him know that you’re genuinely concerned for his future. Should anything at all go wrong, he’ll lose everything. If you’re really looking to put some effort into helping this guy out, you can offer to help through a job search process. Again, this will only work if he’s actually looking for help.

If he doesn’t ask for your advice, then there’s not much you can really do here except slap him upside the head and tactfully inform him that he’s a douchebag. He’s going to keep leaching off this chick as long as she lets him. And if you’re thinking you can get to this girl, it’s still not going to happen. If this guy is as much of a loser as you make him out to be, his girlfriend’s mom/dad/sister/brother/best friend neighbor/mailman has already informed her of that fact and she’s already chosen to ignore their (non-solicited) advice.

If you had one of these two characters writing in asking for my advice I’d have something entirely different to say, but that’s not the case here. As long as neither of them are asking for your help, you’re not winning this war so you’re just going to have to let it go.

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