The Bro Code
I have this close friend, who I am really in to, and I think he reciprocates. The natural next step would be a sexual relationship and I think that might be what is holding us both back. My ex is his best friend and I'm close with his ex as well. I don't think that either of us is looking for anything serious, so it might end up being just sex, but I am worried about our friend-cestious sexual history getting in the way of anything happening. I guess my question is should I just skip it and try to look for something more substantial and less complicated with someone else?
well, u can still have a sexual relationship for a while without telling anyone about it, u dont owe anyone to know everything about your life. Or u can try to find out how they would be feeling about it without asking directly, or start a sexual relationship with someone else.
This is tricky. When it comes to my friends, I always try to put myself in their shoes and think about how I might feel if I were in their position and found out. If you are okay with that potential outcome, then I think you are okay to go ahead with it (as long as he is also on board). But if you feel like it may ruin the friendship (or multiple friendships), then you should evaluate whether a non-serious relationship is really worth that risk. Not only that, but if this turns sour you may also be left without him as a friend either.
You mentioned that you are really into this friend of yours, but said that you don't think you're looking for anything serious. I think that before you go forward with this you should really evaluate what you want to be the outcome of this. It does sound complicated...and there are 3 people in addition to you who might end up getting hurt. So I would suggest treading lightly.
I do not advise trying to have a sexual relationship and concealing it from your other friends/exes because if and when it does come out, they will be more hurt. As Kristen said, you are risking losing ALL of these people as friends. Many people do not take well to you dating their ex, so please evaluate how important their friendship is before you create a big mess.
anything worth doing is worth doing openly.