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Dear Breakup Girl,

Okay, I've got a two part problem.

Part 1: I've been in a relationship for six years (five living and moving around the country together). The relationship was supposed to be a one-night-stand (from both parties) but somehow (don't ask how, cause I don't know), it became more. The six years have been rocky. We've always blamed our internal problems (communication, sex, etc.) to outside influences and stresses (moving, bad jobs, etc.). But what I've come to realize is that we're simply not compatible. I realize that the relationship is inevitably doomed. I love her, but I'm not in love with her. We simply don't get along (most of the time). I've been feeling like this for over two years, and it's steadily getting worse for me. What should I do? She's extremely sensitive. (She cries during Hallmark commercials.)

Part 2: Here's the kicker... (Disclaimer: Part 1 started long before Part 2.) I think I'm head over heels in love with a coworker. She's beautiful, intelligent, charming, and eight years my junior. Although I'm not officially her supervisor (we have a flat structure), she does come to me for much of what we do. She and I are 100% compatible in every respect, except age and physical appearance. (She's beautiful; I'm just okay.) Also, we're good friends in the office environment. She knows about my relationship but has no idea about the problems. My problem is:

a) How do I find out if she feels anything romantic for me without screwing up our friendship and without me looking like a complete loser?

b) How do I get Part 1 done and not lose an opportunity with Part 2? This is the clincher. I know breaking up will take time, but in the meantime, my coworker is single and (apparently) searching. Help!

--Stressed

Dear Stressed,

Ah, so the one-night-stand has given way to the six-year-itch. Well, Stressed, I'm sorry about the doom, and I know you must dread hurting your girlfriend. But "extremely sensitive" is not a good reason not to break up with someone. What, hardy souls aren't hurt?

At least -- and I realize this is a weird thing to cite as good news -- you can cite visible, perhaps undeniable problems, as opposed to lopsided, slippery gut feeling. And on the level of mutual (in)compatibility, not individual fault. (Right?) Your job is to be gentle, clear, and firm -- and not let guilt suck you into prolonged after-care. There's more guidance for you here. And here. (Oh: don't send a card.) Honestly: good luck.

Love,
Breakup Girl

PS: Hey! I didn't even mention the coworker! Oh, I know. That's because you owe it to everyone involved -- yourself included -- to clean up (1) before making your, er, lateral move on (2). I know you can't control your feelings in this department, but you can -- and must -- control your actions. Whether or not the crush is requited is not all that pertinent at this time. What, that's actually gonna affect how and when you handle (1)? Shouldn't. Anyway, if (2) is in her right mind to begin with, she is not going to want to feel like part of your personal severance package. So enjoy the CCF as a fix and a sort of zipless rebound, a maybe-someday buzz, if you like. But keep your priorities in the order of your letter.

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