I have been dating a guy for nine months now. We are both in our late 30s. Things have been pretty good so far and although we haven’t talked about moving in together yet, I spend about six nights a week at his place. My concern is his female friend, J.

Just to preface, I am not typically a jealous person. In fact, I appreciated that my ex’s best friend was a woman, and I myself have several male friends. The problem is that I’m uncomfortable with how close J and my boyfriend are lately. He and J have known each other since high school. She got married right after graduation, and about a year ago separated from her husband. Since then she has been dating regularly but she seems to be making unwise choices, based on what my boyfriend tells me. There is a lot of drama in her dating life, which she frequently discusses with him through regular texts and phone calls. Understandable given their long friendship, and I’m respectful of all of that. He is good about not responding to her texts and phone calls while we are together, so I’m glad he has that respect for me and our relationship.

The part that really bothers me is that she discusses details of her sex life with these guys with him. The reason why I’m uncomfortable with this is because some of the comments she makes to him are things I would never discuss with my guy friends, but would probably reserve for my girlfriends, if I’d even talk about them at all. He’s also mentioned to me before that he doesn’t understand why she is with these guys since she is attractive, smart, etc. I’ve never asked him if he’s ever been interested in her, but he’s proactively offered up a few times that she’s “like a sister” to him, which makes me feel like he’s trying to avert the potential question. My gut is telling me something is off here. To be honest, I’m sure a lot of this could be my insecurity, too. Am I overreacting? I feel as though this could turn into something more between them given their long history together and the fact that she seems to look to him to “rescue” her from these situations, and he seems to be obliging. I just don’t want to get hurt.

– His friend