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Dear Breakup Girl,

I've got a bit of a sticky situation here; I'm on a sports team at school, and we're all really close. I'm particularly close with three other girls on the team in my grade; we're always together. First, there's Jamie, who comes across as a quiet person and tends to keep personal things to herself but is really fun when you get to know her. Next there's Lisa, whom I guess you could call the "All-American" girl. She's smart, outgoing, and insanely pretty. Almost all the guys like Lisa. Then there's Caitlen, whom I've been friends with the longest; she's also quite funny and entertaining. And as funny as the rest of them are, I suppose I'd be called the comic relief, because I find humor in every situation. I guess you could call me the baby of the group, and not just because I'm the youngest. But enough with introductions...

The problem is this: Homecoming is coming up, and there is "competition" for dates. The boy that I am really hoping will take me (I'll call him Jason) is a great guy with a sense of humor the size of the Pacific Ocean; he's always laughing and having a good time. Hence, he'd make a terrific date for a dance, right? Right....as if it were that easy. You see, about nine months ago, Jamie confessed to us that she had a thing for Jason. This was quite a shock, because Jason and Jamie are on two total opposite ends of the spectrum personality-wise, and Jamie never reveals these sort of things. Yes, I know this was nine months ago, but I'm fairly positive Jamie still likes him, more than ever. So, even if Jason and I were to go as friends (since we really are, anyway), I'd still feel like I was hurting Jamie.

Oh wait, we're not done yet! There are a few more twists to the story: a few weeks before school started, Jason told his best friend Damian (who happens to be Caitlen's boyfriend) that he really, really LIKEliked (who else?! but) Lisa! So as word got around, and I told Lisa myself, she made it clear that she strictly wanted to be friends with Jason and that Jamie was not to find out about any of it. She figured Jason would eventually stop liking her. (And honestly, I have no idea if he has, but....)

Just the other day, Caitlen and Damian got the notion that they were going to try to hook Jason up with someone. Seeing as he's never had a girlfriend, he wants one, and things with Lisa just weren't looking so hot. And who came up, but good ol' me, Kris. They figured with our wildly humorous personalities, we'd go great together (which I admit, I've thought many times before). And now I'm fairly positive that Damian told Jason that I like him.

So now Jason's acting all "Ooooooh-I-know-you-like-me"-ish, and I must say that while I enjoy it and hope it will lead to a Homecoming proposal, I still have an issue or two to deal with. Namely, Jamie. Seeing as Jamie practically never likes guys (or cares to share it with us) and has liked Jason for so long, I feel so guilty about liking Jason. Please give me some of your wondrous advice, oh wise Breakup Girl!! And as quick as possible, too, because Homecoming is in October!!

-- Kris

Dear Kris,

I would say this is like an episode of Young Americans, but this is like eleven episodes of Young Americans, and I don't think there are eleven episodes of Young Americans. In any case, I'm impressed. It's like "word-spreading" is part of your cross-training. I didn't know you could letter in Gossip!

Okay, I'm totally teasing. I know there are serious feelings at stake here, and you are most considerate to ask about how to spare them. So here's what I think is kosher.

Jason sounds way dreamy. I know you have every reason to LIKElike him. And, as you've said, he sounds like a terrific date. But in a sense, that's all you've told me. As in: you've not told me that he's been your secret undying passionate all-consuming love since, like, before Justin Timberlake. And for your pursuing him to be worth the risk of hurting Jamie, it's gotta be one of those things. So I can't necessarily green-light your making an overt move on him.

That said, if he comes to you, I'm not convinced that you have to be the big martyr and say no just for her sake. I know there's no "I" in "TEAM," but there's no "IF I CAN'T HAVE HIM NO ONE CAN" in "TEAM," either. You'd just have to be extra super-duper varsity considerate. Like, don't play dumb. Take her aside, tell her the deal. And that if that does indeed hurt her, you are so way so way so way sorry. And then never, ever (a) rally her for group dates, or (b) blow her off for Jason. And if Caitlen and Damien still have some time on their hands, get them to work on someone for Jamie.

Love,
Breakup Girl

NEXT LETTER:
Cool dance, bad date: Can I say no now?