Dear Prudence,
I’ve been good friends with a co-worker for many years. I’m a married woman, he’s a single guy, and over the years it feels like our lives have become so intertwined that I never get a break. We go to the same gym, he travels with my family and friends, and he has generally become a part of my social circle. He’s had some difficulty with boundaries and has slept with several of my married friends when they were going through rough patches in their marriages. I’m not worried this will happen to me, but I find that behavior really troubling. He justifies it by saying their husbands weren’t treating them well enough.
He’s also not shy about criticizing my husband, who’s supposedly his friend. His last affair with one of my good friends was really a breaking point with me, and I’ve stepped away from our friendship over the last year. I changed gyms and stopped socializing with him. The problem is that we still work in the same office. He keeps IMing me to ask when we can get together and discuss the “disconnect” he’s been feeling. I don’t really want to talk to him about it. I feel drained (I just lost a loved one this month) and don’t want to deal with him. What’s my obligation to him, and how can I best extricate myself from this situation? He is very emotional about our friendship, so I’m afraid to just tell him I’m done. I should note that my husband is aware of all aspects of my friendship with this guy, including his affairs, and it’s not an issue in our marriage.