When do I [25 F] tell my ex-boyfriend [25M] of 7 months that I slept with his best friend?
Throwaway as some involved know my username.
When, if ever, do I tell my ex boyfriend I slept with his best friend?
Back story: Anthony and I met during college, and dated for about 7 months. We liked each other a LOT, had the occasional bicker but over all very good relationship. Towards the end, things sort of petered out. No bad feelings towards each other, except some sadness and frustration that it was not working. We just both had other priorities at the time. We both felt like things were not fully over, and that there was more to “us” than where things were left.
Anthony and I had essentially zero contact for the next six months, just occasionally waving hi around campus (different friend groups, big school, we barely saw each other). Then one night I ran into his best friend, Kyle. We were pretty friendly while Anthony and I dated but never hung out alone or anything. Well, that night one thing led to another and we ended up hooking up.
I did not and still do not feel particularly guilty about it. I had no commitment to Anthony anymore at the time. However, I recognize that it was a douchey thing to do and if Anthony knew, he would be upset. Kyle felt very guilty as Anthony was (and still is) his best friend. He never told Anthony and to this day I am 100% sure Anthony does not know what happened. That was the only time anything ever happened. We all graduated soon after that so I have not seen either of them since. Kyle and I have not talked since then.
Fast forward to now: Almost two years later after that night. Anthony and I live about 4 hours apart, but recently have begun talking a lot. Nothing has been flat out said but he is clearly trying to feel out the possibility of us rekindling something. I would be open to that. I will be in his city for work in two weeks and plan on seeing him. (And there is a good possibility of me moving near him within the next six months, totally unrelated to him, but that would make a relationship more likely/possible.)
Now my question. Do I tell him? My thinking is this: if I tell him immediately, and nothing was/is going to happen with us, it is causing him unnecessary pain. If we aren’t going to be anything again, it doesn’t seem like he needs to know. (But this is where I’m not sure-maybe he should know regardless?) On the other hand, if I wait and do not tell him now and things begin to progress with us, he probably should know, right? I think he deserves to know and be able to use that knowledge as an “out”, a reason to not date, if he so chooses. But I don’t want things to get too far before he gets to know.
Basically, I think he should know if we are going to date, and if so it should be ASAP, but I don’t want to tell him too soon if we are not and it would just be useless pain/hurt for him.
Also, I have not talked to Kyle about this at all. I’m not sure if I should do that, either. He and Anthony still are friends, but now live across the country from each other so are not hanging out with any regularity.
tl;dr: I slept with my ex’s best friend after we had broken up. Now there is a chance we will get back together. Do I tell him, and if so, when?
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