I'm a little hurt that my question was skipped over in this weeks column. Here it is again:

I am a woman in a heterosexual relationship, about 4 months long, and.... I would like your advice, obvoiusly! It's my first serious relationship, same with my boyfriend. He's never had sex before. We've tried to have sex a bunch of times, but each time something goes wrong. The first time he couldn't get it up. Sigh. Subsequent times, right when he's about to "enter" me, he comes. I have lost passion in and out of bed and I can't tell if it's due to all the sexual let downs. I don't know if I should seek to "fix" the sex thing first or break up with him before we actually have sex for fear that he will get more attached and then I will realize I don't really have any feelings for him.

Questioning Unsatisfied Anxious Little Me

My response after the jump...

First off, QUALM, your letter was one of hundreds that I skipped over last week. I get more questions than I could ever hope to answer, I'm sorry/grateful to say. and while I realize it must suck to send your question in and wait for a response that never comes, QUALM et al, that's the risk you run when you turn to a sex columnist for free advice instead of seeking out the counsel of a hundred-dollar-an-hour shrink.

As for your question... if the sex is lousy/non-existent at four months and you could take or leave the guy, QUALM, you should probably leave the guy. If you wanted to be constructive—if you wanted to leave him in better shape than you found him—it might help if you two de-prioritized vaginal intercourse, which is clearly terrifying and/or overexciting him, and got each other off in other ways, i.e. oral sex and mutual masturbation. Maybe with a few dozen mutually pleasurable sexual experiences under his belt, and the sense of closeness and trust that a series of successful experiences might create, your boyfriend would be confident enough and skilled enough to "enter" you successfully. But if you're not willing to invest that kind of time and effort in him—if he's not worth it—end it now.