Dear Donna,

I recently signed up for a two-week group biking trip. A man who dated one of my best friends also happened to sign up. It had been several years since we had seen each other. Long story short, we developed a great connection over the course of the trip. When I told my friend what happened, she was very upset and, although their relationship ended five years ago and she is now with someone else, asked me not to date him. I don’t want to lose her friendship, but I think he could be someone special in my life and I want to get to know him. She said, “Girlfriends don’t date their girlfriends’ ex-boyfriends.” Help!

Dear Help,

Most girlfriends probably wouldn’t want to date their girlfriends’ ex-boyfriends, but there are always exceptions to the rule. This was not something you planned; it just happened. You should make sure the “connection” you felt on the trip is still mutual and then try to have another conversation with her. Give her some time to digest the news and she might feel differently.

Dear Donna,

I am a single fellow and I find myself very much attracted to Jane, and I think she is attracted to me. About a week ago, Jane and her husband separated. I don’t want to hurt my chances with this very special woman. When would it be proper for me to ask her out? I am waiting with bated breath.

Dear Waiting,

You should wait as long as it takes for Jane to make the first move. People often separate with hopes of eventually working things out. If she is interested in you, she will get the message to you when the time is right.

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Donna Shugrue owns Perfectly Matched. Her column runs biweekly in Home and Family. Visit perfectlymatcheddating.com or email questions to donnashugrue@comcast.net.