Thoughts about dating a friend's ex...

So, background...

My best friend and I met in undergrad and while there, she met her ex, who she dated for the four years of undergrad and split up shortly after breaking up.

I was always good friends with the ex, but never, ever in an inappropriate way. No flirting, nothing. But we kept in touch after the break up because we had similar friends circles, and eventually started flirting here and there - a year or two after they split up. We had some strong chemistry and almost hooked up once but I put an end to it, probably because I was younger and scared.

This went on, on and off, for almost ten years... In between, we would go a while not talking or keeping it platonic when we were in relationships with other people.

Both of us recently got out of serious relationships and started talking more and more. I have never been a casual sex/FWB kind of person, but I finally decided to give it a try with this person because there is trust, connection, and communication. So, that's been happening and it's great. The chemistry, the sex, sense of humor, emotional support. It's casual, but damn, is a lot of fun. The thing is, I can see myself actually developing more serious feelings for him over time.

One of the biggest things that terrifies me about all of this is that he's my best friend's ex! They have now been split up for 10 years and she's been in numerous relationships, including a very serious one currently that will likely develop into marriage. I think she cares for her ex as a person and they have seen each other at social events without it being weird. I just don't know how she would feel about any of this. She knows I've kept in touch with him over the years and hang out with him on occasion, but I've never let on anything else.

I guess I'm just curious on what others thoughts might be. Am I a shitty friend? Or would the time frame kind of cancel that out? I don't think I'll ever really let her know anything if him and I stay super casual, but I guess I'm just pondering like... What if this does start to turn into something? How the heck would I address this with her, and would she be right to disown me over it? I don't think I could end our friendship. I'm pretty sure I would sacrifice the potential relationship... Sigh. No big decisions to make at the moment, but like I said, just kind of pondering the whole situation. I can't shake the feeling that I'm breaking some kind of girl code, which is dumb.

Submitted August 25, 2019 at 11:30PM

So, background...My best friend and I met in undergrad and while there, she met her ex, who she dated for the four years of undergrad and split up shortly after breaking up.I was always good friends with the ex, but never, ever in an inappropriate way. No flirting, nothing. But we kept in touch after the break up because we had similar friends circles, and eventually started flirting here and there - a year or two after they split up. We had some strong chemistry and almost hooked up once but I put an end to it, probably because I was younger and scared.This went on, on and off, for almost ten years... In between, we would go a while not talking or keeping it platonic when we were in relationships with other people.Both of us recently got out of serious relationships and started talking more and more. I have never been a casual sex/FWB kind of person, but I finally decided to give it a try with this person because there is trust, connection, and communication. So, that's been happening and it's great. The chemistry, the sex, sense of humor, emotional support. It's casual, but damn, is a lot of fun. The thing is, I can see myself actually developing more serious feelings for him over time.One of the biggest things that terrifies me about all of this is that he's my best friend's ex! They have now been split up for 10 years and she's been in numerous relationships, including a very serious one currently that will likely develop into marriage. I think she cares for her ex as a person and they have seen each other at social events without it being weird. I just don't know how she would feel about any of this. She knows I've kept in touch with him over the years and hang out with him on occasion, but I've never let on anything else.I guess I'm just curious on what others thoughts might be. Am I a shitty friend? Or would the time frame kind of cancel that out? I don't think I'll ever really let her know anything if him and I stay super casual, but I guess I'm just pondering like... What if this does start to turn into something? How the heck would I address this with her, and would she be right to disown me over it? I don't think I could end our friendship. I'm pretty sure I would sacrifice the potential relationship... Sigh. No big decisions to make at the moment, but like I said, just kind of pondering the whole situation. I can't shake the feeling that I'm breaking some kind of girl code, which is dumb.