Dating a friend’s ex

Hello. “Twilight” contest winners have been chosen and will be notified by e-mail. I will post winning entries tomorrow morning. They were all pretty brilliant. One of these days we’ll have a Love Letters event that’s open to everyone, without a contest. We’ll all jump on top of one another and sleep in a big pile (sorry – that’s from “Where the Wild Things Are,” which I saw this weekend). Here’s today’s letter. Let the wild rumpus start.
Hi Meredith, My question today is about friends and dating past boyfriends/dates of your friends. Here is my situation: I am single and in my early 40s. The guy, let's call him Kevin, dated my friend, let's call her Mary, for about 2 months, about a year ago. I only met him a few times while he was dating my friend and did not know him well at all. I have recently run into Kevin on several occasions. We have some mutual friends, other than Mary, and have lots of similar interests as well. On the third random encounter, after an evening of nice conversation, Kevin asked me out. I told him I'd have to check my calendar before accepting, but that I was interested. I really didn't need to check my calendar, I am not that busy. What I needed to do was check with Mary. I had an honest, direct conversation with Mary - I told her I had run into Kevin a couple of times, that we had really hit it off and that I would like to catch a show with him next week. She expressed no objections, and in fact seemed enthusiastic and happy that we had connected. Fast forward about a month...I have had several dates with Kevin, things are going well, and we are considering going away together this weekend. I told a mutual friend of mine and Mary's, and she told me that Mary has been talking to her about the situation and is NOT happy that I am dating Kevin. I tried to have another conversation with Mary about it, but again, she made no objections. My question is ... Should I break it off with Kevin before it gets serious? Do I owe my friend this courtesy since I know she is upset about it? Or, do I continue what is a very nice, respectful, fun dating relationship with Kevin? I am happy with the way things are going with Kevin, and very unhappy with the dishonest response I am getting from my friend. Some information that the LL crew might need: - Mary is in a long term relationship that has been off and on for 3 years. She was on a "break" when she dated Kevin and then went back with the guy she is currently with. - Mary has a tendency to use men. She likes to have a few on the back burner to call when things are off with her steady bf. - Mary is a good friend. We call a few times a week and I usually see her at least once a week. - Kevin has the potential to be a long term boyfriend. He is not a fling, and although I am taking things slow (I have not slept with him yet), I am becoming fond of him and I can see it developing into more. - Mary and Kevin dated for 2 months, they did sleep together, but no "Love" words were exchanged.

– Trying to be a good friend, Boston

TTBAGF, It's a little too late to undo your relationship with Kevin. If you dumped him now to please a friend who is in a committed relationship with someone else, you'd resent that friend. Your relationship with Mary would be at risk. All you can do is move ahead with Kevin and take Mary at her word. If she says she’s dealing with it, she probably is. Many readers are going to tell you that it's never OK to date a friend’s ex. I’m mostly with those readers -- but not always. It’s never an easy choice, but you have to be a good friend to yourself sometimes. (And yes, I’m factoring age into the equation.) Mary is in a relationship. She wants you to be happy. She has the right to feel weird about you and Kevin – it’s normal to feel strange when your friend dates a man who has seen you naked -- but I would hope that Mary’s love for you would trump that weirdness. Tell Mary you adore her. Tell her you're going to assume that she has told you the truth about her feelings. And tell your other friend – the middleman – that all you can do is deal with Mary directly. Go-betweens are never very helpful. Maybe Mary was just using the go-between friend to vent. Maybe she just wanted to shout for a bit to get the weirdness out of her system. That would make sense. I think you've already made a choice. All you can do now is to go out of your way to be respectful. Readers? I know we all have strong feelings about putting friends first, but … it sounds like this reader thought she had permission. Is Mary being passive-aggressive? Is the go-between friend causing trouble for no reason? Is the letter writer in the wrong for pursuing this to begin with? Share.

– Meredith