Mr. Perfect’s coming home on November 23, 1998…

Dear Breakup Girl

Found your site when I had just broken up with a guy I dated for 7 years and it gave me some good laughs along with some good advice, so thank you…

Now I’ve gotten myself into this really weird situation and I’m not quite sure how to get out of it…or if I want to get out of it. After this breakup, I was feeling pretty down in general amd wound up taking comfort in the arms of this incredible guy…we had a little bit of a summer fling…which was actually great, my self esteem got a boost (this boy is beautiful) and I had a great time…then he went back to school (he’s 22, has one semester left at an almost Ivy League school, will be done in December and back in town, I’m 24, working in a big city, real life kinda crap).

Here’s the kicker — I’ve known Mr. Perfect for about 10 years…he happens to be my best friend’s little brother…and we chose not to let my friend in on this little fling because we weren’t sure how she’d react…in fact, our parents are friends with each other, and they have no idea either.

So we had this summer fling, that even had a little snag in it when I went up to visit my friend at their family’s summer house and the three of us spent the entire weekend together and we continued to hide the whole thing…well, we just stayed away from each other…then when we got back, we decided we shouldn’t continue the fling because it was too weird (he’s almost like MY little brother –we used to beat each other up…it was weird for him to look at his sister and difficult for me to look his mother in the eye, considering what I was thinking about her son…).

Well, that lasted about a week, until we went out to lunch and scrapped the idea of staying away from each other…it’s just too much fun…that was in August.

He went back to school, and we’ve kept in touch via e-mail (I hear from him more than I hear from his sister) and unfortunately, I’ve been thinking about him NONSTOP since he left (not impeding dating other people, just whenever I’m not thinking about anything in particular, I’m thinking about HIM).

He’ll be home next week for Thanksgiving, and then permanently after Christmas…his sister won’t be home for Thanksgiving (good AND bad) and we (me and Mr. Perfect) have tentative plans to get together. The thing is, we’ve never actually talked about what this little thing actually is — at first, it was more of a rebound fling for me, and I just figured it was kind of one of those things for him where he was finally getting to see what it was like to be with his sister’s best friend (he was a little puke when we were younger, always trying to get in the bathroom when I was in the shower, etc….I have a hard time remembering the exact point where he went from being a little puke to being a smart, beautiful, sweet, datable guy).

So anyhow, I have no idea how he feels about me, and I don’t know how to bring it up…I’ll probably see him over the Thanksgiving break, maybe a movie or something, or maybe more….I don’t know. But I KNOW I have real feelings for him and I need to tell him and see what happens or I will regret it forever. I’ve even come to terms with the fact that I will have to tell his sister about it and just deal with the consequences…I think she’d be a little jealous at first, but would get over it eventually. I just didn’t want to tell her if it wasn’t going to turn into anything).

Any ideas on how to begin THE TALK?

— In Love With My Best Friend’s Little (6’3″) Brother

Dear In Love With the Little Puke,

If he’ll watch Babe with you, he’s a keeper.

Other than that, hmm. Maybe you’re entranced by the weirdness and danger; maybe this is one of the many wild and wonderful ways lasting couples [re-]find each other. Whatever. If you need to speak your piece with him, speak away. There’s no one right “how to” here — though I do recommend keeping things on the lighter side (like, don’t slip up and add “in-law” to any mention of his mother). Something like, “So now that you have a vocabulary that includes words other than ‘puke,’ ‘boobies,’ and ‘booger,’ what would you call this thing?” And remember, In Love, you told me yourself that the point of asking is to preempt regret (as opposed to: to get the Right answer). So you can’t lose. Right?

For my money, though, the speech you really need to rehearse is the one you may have to make to your best friend. I know say you’ve “come to terms” and are prepared to “deal with the consequences.” You may be, but that doesn’t mean she is. Who knows, maybe she’ll say she saw this coming ever since her brother drilled that peephole in the bathroom wall. But it’s also possible that this will strike her as the weirdest most undealable turn of events ever. Not for any rational logical reason — there’s no true, like, betrayal here, but still. It’s her brother. Don’t underestimate. I just want you to be prepared — just in case — for her to remember the exact point where (in her eyes) you went from being a smart, beautiful, sweet gal to a little puke. If that happens, yes, she’ll probably get over it. But I want you to be just as careful about keeping this relationship as you are about hiding the other.

Love,
Breakup Girl