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Dating My Ex's Friend

"Is It OK to Date My Ex's Best Friend?"

This question is from a Group Therapy post in our TrèsSugar Community. Add your advice in the comments!

My ex and I dated for two years, and we've been broken up for another two. We don't keep in contact, even though I do occasionally receive angry emails from his baby mama, but that's another story. Basically, though, my ex and I have nothing to do with each other, and it's a dead story.

During our relationship, I did hang around his best friend occasionally but I always felt like he didn't like me. We never really took the time to get to know each other and I honestly didn't pay him much attention. After the breakup, there were times when I still hung out with my ex, and there was one night when all three of us went out to a bar. My ex was completely MIA the entire night, so I hung out with his best friend. We spent the night chatting and getting to know one another, and all in all, I had a great time.

For the past year, we've been keeping in touch on and off, and he confessed that he's always had a thing for me but couldn't express it out of respect for my ex. I always thought he was attractive but never paid much attention to it. Now that I'm single, though, I am well over the disaster of my past relationship and I wouldn't mind getting to know him on a more personal level. A part of me thinks it's OK, but on a different level, I think it's wrong. My past relationship ended so horribly, and that's why I try to distance myself from anything that has to do with him.

I think I'm just afraid of drama coming up if my ex gets wind of what's going on between me and his best friend. I really do like this guy and I'd like to see where it might lead, but I'm very hesitant. He lives two hours away from me, and I've agreed to go spend a few days with him. What do you think? Should I take the chance or look elsewhere?

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Donna-Freundt Donna-Freundt 3 years
I guess you have to figure out if you think the drama - risk is worth taking. If your ex can still have a friendship with his bf, and let you two have your own separate relationship together without being involved. Personally I would not do this.. I would think it is healthier for myself to be away from my ex and to find someone who isn't connected to him. Especially if the relationship ended badly. I think though this is only a situation that you can judge and that it wouldn't be completely impossible for it to work out. Good luck, if things get bad you can always end the relationship and stay away from both of them.
henna-red henna-red 3 years
You seem to understand intellectualy the risk here. Being back in the environment that includes your ex, and that means possible also, his baby mama. Are you ready for that? Is you're ex's BF? Have you discussed that? This is a very sensitive boundary issue.....and you describe this guy as your ex's BF...that's very telling for me. It's a label that tells me this friendship is very important to him, so do you think he can maintain a relationship with his BF and with his best friend's ex? Can he keep those relationships seperate? balanced? Can he have you in his life, without drawing you into the circle of his friendship with your ex? Personaly, I think, your connection to this guy has to be impossible to ignore in order to persue this potential relationship. I have trouble believing that this will not contain big drama at some point. And I think you know that too, so my question is .... are you into the drama, even though you say you're not? I think your words and your actions are not lining up....your actions are heading you towards drama. They are heading you towards the people you have spent time getting away from, and it makes me wonder if you are somewhat of a drama junkie. I think the whole issue rides on the BF's ability to maintain really strong boundaries....and I have my doubts. You say you're hesitant, but I don't believe that....because you've committed to new year with him. That's not casual. I think you're heading into this, and I just hope it's with eyes wide open. Right now, I don't think that's true. Good luck with your choice. happy holidays
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