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March 16, 1996

A few months ago I met a wonderful woman. Unfortunately, she was dating a good friend of mine. He dumped her two weeks ago. When should I ask her out with a decent chance of her not saying no because I am a friend of the louse who dumped her?

Just like a guy to think there's some kind of clock. T-minus 200 hours and counting! It's an emotional thing, get it? If he dumped her, she's probably somewhat wounded. Even if she's got confidence like a rock, a part of her is saying, "What's wrong with me?"

Stop thinking about how you can control the situation. Give it up! You won't know how she feels about the breakup, or how she feels about you, or anything unless you plain ask her. If you've read any of my advice before, you know I'm really big on the "H" word.

Tell her that you feel really embarrassed by what your friend did. Tell her she seems like a wonderful person and you hope she doesn't find you guilty by association. Ask her how she feels.

That last point is important, so read it again. You don't have to say, "I want to be your friend." Just be one. Be a good listener.

If she's giving you the cold shoulder big time and you want to break the ice, send her a card with a picture of yourself and a donkey. Write:

Yes, he's my friend. But I hope you don't think that makes me an ass, too! Can I change your mind?

I keep getting pebbles in my shoe. What should I do about it?

Apologize and return them to their homes.

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