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Dear Breakup Girl,

I need some advice that could determine the fate of a friendship! My best guy friend just told me that he liked me and he asked me out, even if I couldn't imagine a relationship with him! The problem is, though, one of my really good friends likes him!! If I say no to him, it'll save my friendship with my gal pal, but it'll emotionally crush him (because he's never asked anyone out before). But if I say yes, she'll be really upset (considering the fact that I'm her friend), but he'll probably build up more self-esteem or something like that. What should I do??

-- Lissy

Dear Lissy,

Let's say your friend liked this guy AND you rilly rilly rilly rilly liked him too. Like, rilly. If he asked you out first, it would be painful and icky -- yet still legal -- for you to date him ... as long as you were gently up front with your friend rather than doing your business behind her back or in her face. I mean, when people attend school/hang out in small or finite numbers, dating overlap happens.

But it doesn't sound to me like your feelings for him are of the "You are my fire, my one desire" variety. So as upset as your gapal might be to find out you were dating him, she'd be that much more upset to find that you were doing so ... without really LIKEliking him.* Likewise, as upset as he might be to for you to say "no," he'd -- ultimately -- be that much more upset to hear you say yes ... without really LIKEliking him. It's the opposite of what you say, Lissy: Mercy Dating is -- again, ultimately -- more of a self-esteem killer than, say, a graceful, grateful "No thanks." Or maybe even a "No, thanks, I can't imagine a RELATIONSHIPrelationship with you ... but I know someone who can ...".

Love,
Breakup Girl

* for an example,, see "Never Thought I'd Do It," below.

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