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Dear Breakup Girl,

I have this friend (no, *really*) who went through a very complicated and icky breakup last spring. "Mary" had been with "John" for something like seven years. They met in college, and had been doing the distance thing for the last few years as they both worked on graduate degrees at far-flung universities. In the year or so previous to the breakup, John had begun to pressure Mary about marriage. He saw all their friends from college beginning to settle down and tie the knot, and felt it was time for him and Mary to do the same. Mary, however, felt unsure. About everything: she was unsure whether she ever wanted to be married to *anyone*, she was unsure about whether she wanted to marry John in particular, and she felt that no matter what she did marriage-wise, she really needed to complete her graduate degree and begin her career first/too. John began asking her why she valued her career and her studies over their relationship (though of course, he never considered the possibility of dropping *his* studies or moving to be with Mary; it was only talked about in terms of Mary moving to be with John). Mary began finding herself attracted to other men. And in fact, she carried on a brief fling with a guy we both know--a guy totally terrible for her, who could never be a real boyfriend, but who made her feel attractive and gave her something interesting to look forward to, instead of the usual fights with John about her career versus marriage.

Now, Mary had been expressing to me all along real ambivalence about John. She was starting to be un-attracted to him. The fling with The Other Man certainly helped that feeling along. She was really looking around, a lot, at other options. And then, It happened. John dumped Mary. Mary couldn't believe it--all along, it had seemed that if one of them was going to give the other one the boot, it would have been Mary dumping John. But John declared he couldn't take it anymore, he didn't appreciate coming in second place to her studies and career, and he needed to move on.

Here's where the problem comes in: over half a year later, Mary is still miserable. And, perhaps more to the point, she is beginning to make me miserable. Mary is a wonderful, smart, funny, attractive woman. In my opinion--and I have told her this--the breakup with John was ultimately for the best, given her clear ambivalence toward him, the fling with The Other Man, her more and more frequent crushes on other men. I just thought these things were a sign that she was ready to get out of the relationship, but she just couldn't bring herself to do it. John saved her a lot of guilt by being the one to drop the axe himself.

Unfortunately, though, that axe-dropping has only served to make Mary feel like a reject, a loser, a hideous thing destined to live her life alone. She comments on this regularly. We hang out together at least once a week, and every single time we get together, she makes at least one (but usually more like 4 or 5) self-pitying, "I will never find a man and am destined to die alone" remark. Along with reminiscences about John, occasional hopeful remarks that one day they might be together again, sad commentary on all the things she can no longer enjoy because they remind her too much of her relationship with John. Oh, and jealous, "I hate them" remarks about anyone we know who's deliriously in love. I mean, who can blame her there, deliriously-in-love people can be annoying, but she seems to see every relationship to be an affront to her personally.

I want to be a good friend to Mary, and I want to help her through this. But I just don't know how to do it. I've tried countering her self-pitying remarks with compliments, but she rolls her eyes. I try countering her "I will never find a man" remarks with encouragement, suggestions for places to go where there might be eligible bachelors, reminders that lots of people go through a dry period and it doesn't mean it's the end of the world (though I sure know it can feel that way). I try to counter her reminiscences about John with reminders of all the reasons the breakup was really a Good Thing, but she frequently ends up defending him. I just feel like I can't win, and this breakup is making her so miserable that I'm a little nervous about being with her. I feel I'm inadequate at supporting her because I can't think of anything to say or do to make her feel better, but I also feel a little angry at the way she's wallowing in this and making *me* feel defensive and uncomfortable. So, I guess I have some questions for you:

1) Do I have the right to silently wish she would cut it out? Or am I being a bad friend?

2) How can a good friend help someone through this kind of thing? I feel like I've tried a few different angles but she's not happy with anything I say when she starts wallowing. I've even tried suggesting that we really do some research and find some fun places to go where she could meet someone, but she tends to make a caustic remark at that point, so I let it go. She does have other friends (in fact, many more friends than I have--one of the many things I am frequently tempted to remind her that make her a very fortunate person, along with good health, tons of brains, and a lot of money to boot) with whom she goes out regularly to bars, parties, etc. So she isn't sitting at home by herself; I just think her attitude might be standing in the way of her finding any happiness, either with or without a new boyfriend.

3) Am I actually a *bad* friend for not telling Mary how I feel? Part of me feels that it might do her some good if I had an honest, non-accusatory, non-judgmental little discussion with her about all of this, but I also worry that I might hurt her feelings and I don't want her to feel even worse than she does now. I really just wish she would recognize all the blessings she has in her life right now, boyfriend or not, and also understand that the more she obsesses over how unloveable she is or how unlikely she is to ever have another boyfriend, the more likely those statements are to be true.

Or should I just cut her some slack? Trying to do the right thing --

-- Iseult

Dear Iseult,

"Mary, Mary, quite contrary, how does your garden grow?

'I will never find a man and am destined to die alone.'"

Contrary, indeed.

You're definitely not being a bad friend, Iseult -- hey, you wrote, right? -- but clearly, your lines aren't working, either. Countering, arguing, cheerleading: no. Miss Contrary is not interested in feeling jauntier right now, and you can't make her. But here are some other options to try.

1. Make one speech. Tell her it's the only one, and then you will drop it. And so, you request, will she. Tell her that that "I'll die childless and alone" feeling is normal and understandable. But ideally, it is a feeling, not a platform. And not, we hope, the seedling of a big prickly venomous un-fun self-fulfilling prophecy that's going to choke out everything else in that garden. Yanking that weed would be an excellent idea. Angst is not attractive to friends, or to potential boyfriends, unless you are Rose MacGowan. But she knew that.

2. Agree with her. I don't care what you actually think; just say, "Mmmhmm, yesss, uh huh." Your arguing is just fertilizing Contrary's claims.

3. Don't tell her how to feel, tell her how you feel. Tell her what you told me, complete with why you worried and hesitated.

4. Tell her to write to me. I can say the stuff you can't.

5. And if you tell her you took the time to write to me about her already, she might be a little honored and flattered. And embarrassed. All of which might help her help me come up with a new line that actually rhymes.

Love,
Breakup Girl

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