Dear Darry,

Wow, that is a May-September thing (yeah, as in May 1958, September 1998). Let me ask you this: are you worried about the mother-figure thing in principle, or in practice? I mean, does your concern stem from a vague "Is this weird?" notion -- or from some actual dynamic you guys have (e.g. when he didn't call to say he'd be late for dinner, you took away his phone privileges). Or, for that matter, is there some Freud-oid episode in his past (oh, say, loss of his mother) that might predispose him to seek out a substitute? Or one in your past that might predispose you to be that substitute?

So whether it's "fair" or not really isn't the issue (unless -- and there's no delicate way to say this -- your young lad would like someday to be a dad). And these things can work out. I mean, I'd marry Leonardo DiCaprio in a heartbeat, and I'm technically old enough to be his mother. I know that's totally hypothetical, of course, on account of he doesn't know I exist, but just think of all the new hits this page will get now that his name will turn up on search engines. Breakup Girl is no dummy.

Anyway, the issue is whether the mom-son thing is a problem in the relationship -- or in your mind. Even if it's in your mind, you still need to work it out for yourself before you put the moves on Stud Boy. Your relationship is indeed a tad controversial, and if there's something real there, it has to be real enough to withstand the eyebrows it's going to raise.

Love,

Breakup Girl