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Dear Breakup Girl,

I'm a basically happy, 24-yr-old grad student studying music (performance) and living life in the Windy City. The main drag in my life right now is my inability to turn a close friend into "more" b/c someone else got there first. "Ben" (21) has really become one of my best friends in the past couple of months, and has told me lots & lots of details about his relationship with "Polly." Although I know Ben's a big boy who can take care of himself, I also know that he's not super-experienced when it comes to relationships, and I worry that he's putting up with crap from Polly b/c he doesn't know he doesn't have to. (Which is strange, b/c he takes no bull from anyone.) I also worried about rocking the boat between Ben and me too much, b/c we're in a quintet together, and personal stuff can get ugly when five people are trying to make music together. I've spent a long time wondering whether there was any way I could tell Ben about my concerns about Polly, and whether there might also (instead?) be a way to tell him about my feelings for him.

I stewed over these questions, and came to a conclusion: His relationship was bugging me more than our lack thereof, and I needed to say something. But if I was going to do that, I couldn't be bad-mouthing Polly in order to get my shot at Ben. Not if I wanted to be Ben's friend (which is priority #1 -- there aren't too many people I can talk to the way I can talk to him). So I convince myself to back off on the romantic interest, and be his friend, b/c it was REALLY important to me to tell him how worried I was/am. (Side note: I've never met Polly, so everything I know about her/the relationship comes from Ben. The fact that he can tell me all these scary details and not be scared himself, well this scares me the most, so I wanted to try to hold up a mirror for him, hoping he'd see.)

Enter Tuesday night, a week or two ago. We're on the phone for three hours, during which we have a REALLY GOOD talk, he listens to what I have to say, clearly appreciates that I care, takes me seriously. He was even a little offended that I thought he might be offended! :-) I end up promising to withhold final judgment until I meet her (which should be any day now). And I feel all mature and adult-like to be able to put my friend's best interests in front of my own and get over my extra-friendly feelings for him

Yeah, okay, so THAT lasted about 2 days.

Ben and I go out for a late dinner, during which we get into some interesting banter. At one point, we get talking about throwing each other into snowbanks (we'd had a big snowstorm a few days earlier and had gotten into a snowball fight), and I slip out with a comment about how it would be fun to throw him into a snowbank -- especially if there were no Polly. He doesn't freak, and we laugh it off. Hmm, what's a little sexual tension between friends? And when I see him the next day, the vibe is ... softer. Nicer. Like maybe he likes the idea of me throwing him in a snowbank. Or like maybe I'm projecting.

Weekend starts, my audition happens (tout passe), and my best friend is in town for a conference. Best friend "Alan" bonds with Ben while sitting in the audience at my concert that night, and Ben, Alan and Dave and I go out for a drink (or three) after, with other friends. Way fun night, all my favorite men getting along like gangbusters. But on the way out of the bar, after a frustrating day and too many gimlets (but that's only 2 b/c I'm a lightweight), I make a VERY MEAN comment about Polly. Ben's quiet the rest of the night, as he walks Alan and me back to my place and says goodnight. Alan and I talked late into the night, and he basically said he wasn't sure Ben LIKElikes me, and in any case I need to be more practical. But that's pretty standard advice from Alan, who has known me to project on more than one occasion, and hasn't really seen Ben and me together enough yet to judge well. I also told Alan all I know about Polly, and Alan called it "Jerry Springer" material. Alan can be a bit dramatic, and I think that WAS overstating it, but you get the idea.

Morning comes, I get Alan back downtown, and while treating myself to lunch out, I have something of an epiphany: time to stop feeling sorry for myself that I can't get Ben, b/c I'm not GOOD at relationships. I need to work on this at some point, but in the meantime, I AM good at friendships. I buy a couple of ani difranco CD's and step out in style with my whole new 'tude. And I call Ben to apologize for my evilness the previous evening, and he basically tells me he had already forgiven me b/c I was drunk and had had a stressful day, and that wasn't why he was being quiet, etc. I joke that, since I'm much better at friendships than relationships, I just need a friend I can have sex with (not a proposition, just an off-hand comment, really). Well, Ben stops me in my tracks by halfway making an offer, before laughing it off and saying "no, I don't know why I said that." Yeah, me neither.

So this is basically the situation. I keep trying to get over him, so I can deal with ME needing to figure out what I really want in a relationship, but the more I try to envision Mr. Right, the more he looks like Ben. And I mean really this time, b/c I've been a dweeb about seemingly-perfect men/boys before, and this ain't that. No, really. Meanwhile, there's this crazy eye-contact and this feeling like we just have fun making suggestive comments to each other and we both know that's all it is, and we both know that's not QUITE all it is. The good news is I know he loves me as a friend (not that he's told me, but he doesn't have to), and he knows likewise (I HAVE told him).

Should I hold out hope? Should I push him to reconsider breaking up with Polly (in which case I keep my distance from the him-and-me issue)? Should I just laissez-faire? Help?

-- (Still an) Optimist [more from Miz O. in the Shoutouts]

Dear Optimist,

Here's your bind. You have neither a Regular Friendship with Ben, nor something More. If I thought you were content to enjoy the flirty fizzy buzz of the crush, well, I would tell you to do just that. But you're not. Seems to me that a majority of your "friendship" is spent dissecting and interpreting. Or deciding I'm Not Gonna Worry About The Ben Thing. Which is the same. It's not just being friends. Nor, even, friends-plus.

So what to do? Well, you can't push him about the Polly thing. Intervene directly, and you'll be part of the Jerry Springage. Nor, frankly, do I think you should Talk that much about it when Ben. Your interest in the matter is not entirely ... disinterested. Sounds to me like that's all about finding a way to be close and intimate with him and torturing yourself at the same time. Who-hoo!

If anything at all's your business here, then, it's strictly between you and Ben. Or, to amend that, between (among) you two and the rest of the quintet. Which means that, yes, you do have to be decorous and circumspect. If you want to gently ask him to clarify the deal between him and you, then be my guest (some guidelines available here). That said, though he is flirting with you, it doesn't sound to me like he's ready, for anybody/reason, to write himself out of the dissonant duet he's in right now. So the other thing you could do is gently tell him that actually, you value his friendship and have a little trouble negotiating certain what you take to be mixed messages. So that maybe you could limit the friendship to ... friendship. Just the two/five of you. Like, not Pollyphonous.

Love,
Breakup Girl

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