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Dear Breakup Girl,

I've known a girl for 18 years. She used to be my best friend, but now we're just good friends. I love her more than life itself. I've seen her go through tons of boyfriends and I think it's time for me to ask her to our senior prom. Bear in mind that this would come as a total surprise to her, and I'm not sure that it'd be a welcome one. Sometimes I think that she's too cool for me or something, though she always makes time for me when I need it. How can I test the waters before actually deciding whether or not to ask her? If I told her how I feel and she is turned off, could we ever go back to being the friends that we were before. I'm sooooo scared and I desperately need your help to get me through this in one piece.

-- Drew B

Dear Drew B.,

Oooh, are you Drew Barrymore? In that case, there are many ways in which this invitation would be a total surprise to many people!

Okay, sorry, I'm just teasing. To tell you the truth, I'm not sure that your invitation would surprise her. But what might surprise you, Drew, is that there's a middle ground here that you're not seeing. Asking her to prom and "telling her how you feel" are different. It's not a bended-knee declaration of love; it's an invitation to a fiesta. Which, yes, may imply how you feel, but that's it. So, you're gonna quake in your boots when I say this, but: just ask. Lurking and hinting and sidling and loitering, in the interest of "testing the waters," is exactly what does inflate this from an invitation to a Huge Deal. And by the same token, don't equate her [possibly] saying "no" and being "turned off;" she may just not think of you in Prom Terms. I really, truly, don't think that a simple invitation -- if declined -- would jeopardize your friendship.

That said, kiddo, I'd line up a backup. Not because I can psychically predict your intended's answer, but because it's clear that you, Mr. More than Life Itself, have a lot riding on this. I don't care if your Plan B is to go with an established Friend or a longshot new girl or to plan a fun alternative with other buddies. Whatever. But while you're at it, hey, go plan some stuff with other buddies, regardless. I just want to make sure that -- no matter what she says -- your life matters to you more than Prom itself.

Love,
Breakup Girl

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