Strictly business: Should he ask his lawyer out?

Q: A couple of weeks ago I retained a lawyer for some personal matters. She is a very attractive woman in her mid to late 30s. I am 45. I find myself very attracted to her and would like to ask her out, maybe for some cocktails and a bite to eat.

Of course, I understand that this is a business relationship right now. On the other hand, I’ve sensed that she might be interested as well. I’m a little reluctant to ask her out because if she were to say “I don’t think that would be a good idea,” I think I might feel a little uncomfortable afterward.

On the other hand, I still think I would be able to move ahead with the business at hand. If I don’t ask her, I’ll always wonder what might have been.

Your advice?

Steve: As the Polish partisan said when asked why he was shooting Germans first and Russians second, “Business before pleasure.” Assuming she is ethical (insert your own lawyer joke here), canons of legal conduct prevent her from dating you. Once your business is complete, then she can go out. So be patient. Or get another lawyer.

Mia: Exactly. Although remember how Charlotte on “Sex and the City” switched from a cute lawyer to a dorky one, because she was attracted to the cute one? She ended up getting together with the dorky lawyer. Sometimes mixing business and pleasure works.

Q: An old boyfriend of mine who lives in Chicago tracked me down on the Internet a few months ago. We’ve been e-mailing and chatting ever since. I told my husband about this, and he’s cool with it. It’s innocent and we’re each happily married.

Here’s my dilemma. My old friend is coming to town for a convention and has asked me to dinner. He didn’t mention bringing my husband. It would be fun to see this guy again, but I don’t want to do anything stupid. What do you think?

Steve: There’s a difference between stupid and stoooo-pid. Going to dinner alone with this man is stupid. Doing anything with him after dinner would be stoooo-pid.

Mia: Why don’t you meet him for lunch? Lunch is a much more platonic meal, and there’s less likelihood of anything happening because you’ll have to go back to work.