Dear Breakup Girl,

One of my project partners, who is also a reasonably close friend, confided to me recently that she likes my roommate. They have been best friends for a couple of years, and my roommate asked her out about a year ago. She told him at the time that she did not want a relationship because she was not yet over another serious relationship she had ended recently-ish.

Last night I found out that my roommate still has feelings for my friend, but he’s bitter that she “rejected” him a year ago. They are still close friends, but he cannot accept the idea that her feelings may have changed.

I didn’t say anything, as I am sworn to both of their confidences. However, I think that they would make a great couple and would be very happy together, seeing as how they’re already close. I’ve tried to drop subtle hints to get them to talk about it or at least tell each other how they feel. I’m either not being direct enough, or they are only hearing what they want to.

I don’t know what I should say to whom or if there’s something else I can do. I don’t want to keep my mouth completely shut, because I would feel sad and partly responsible if they never admitted their feelings, even if they ended up not dating. (I may also be biased since my current b/f also started as a very close friend.) Caught in the middle —

— Scythe

Dear Scythe,

If your life were a sitcom, you could do that thing where you invite each of them to have dinner with you, and then only they show up. Sparks fly, hilarity ensues. Of course, if your life were a sitcom, this plot would also go terribly, terribly wrong.

So instead, hatch no plots — but do more than drop hints. If you were a reporter, you wouldn’t be allowed to quote off-the-record material, but you could use it as “background” — that is, to obliquely inform what you do write/say. Pick one friend, and strongly, directly suggest that s/he ask the other out. You don’t have to say why. If you were one of them, you’d hate you if you didn’t.

Love,
Breakup Girl

This advice was originally published November 16, 1998.