Tell Me About It: Friend's become a downer - how to escape?

Adapted from a recent online discussion.

Question: How do friends drift apart if I'm the only one drifting? I have a friend who lives somewhat near me, who I've known since college. We weren't super-close, but I suppose since we've known each other so long, we've kept up this friendship.

I would like it to drift into the ether. My friend is selfish and consistently negative - she constantly complains about how tough her life is, even though she has everything she's ever wanted - i.e., husband, kids, a certain amount of money, big house, etc. I find our (thankfully) infrequent get-togethers draining, and find myself competing with her in complaints to - I suppose, childishly - prove that she actually has it quite good. I then vent about these visits to my husband and friends, and I'm sure they're sick of hearing about them.

I've tried to drift away by not initiating contact, but she always seeks me out eventually. My other friends and husband say I should suck it up and do these quarterly get-togethers, but I don't want to. Is there anything I can do short of a big dramatic breakup? Don't really want to do that, either.

Answer: Why are ending the friendship and "suck it up and go" the only choices on my menu? What happened to telling her the truth?

Each of her complaint sessions is an opportunity for you to say: "You know, I've listened to you complain about how tough your life is - for years, really - but from the outside, you appear to have everything you wanted. If that's not enough, then is it time to look inward to figure out what's missing?"

Win-win, right? She'll either take it to heart or never call you again.

I suppose she could spin your candor into something she wants to hear and then resume complaining, but then you can say: "OK, let's try this: Tell me something positive about your life. We'll talk about that."

If even that doesn't work, two words: theater tickets. You don't talk, then talk about the show. By then, the "dramatic breakup" option might not sound so bad.

Question: I just put my foot in my mouth, and I'm hoping you can help me rectify things. One of my (fairly distant) coworkers has been out all week. He came in today and I said "Hi" and asked if he'd been on vacation. (I know I shouldn't have done that. It just came to my mind.)

Unfortunately he'd had a death in the family. I extended my condolences, of course, but I know I put him in a tough position of having to talk about something he likely wouldn't have brought up organically. Is there anything I can do or say now to apologize, or would it be better to let it drop?

Answer: Yes to letting it drop - your condolences were enough. Bringing it up again would "put him in a tough position of having to talk about something he likely wouldn't have brought up organically" and serve only to repeat the error.

The error, by the way, was one of friendly intent, so don't beat yourself up too much.

Chat with Carolyn Hax online at noon Fridays at www.washingtonpost.com.