One of my female best friends of many years had a fling with one of my male best friends, “James,” a few months ago. They were never in a relationship and only met up twice (they did sleep together once) before James cut it off and they both agreed that they didn’t want anything serious. After it happened, I asked my best friend how she felt about James, and she kept saying that she did not have real feelings for him.

James and I had kissed a few times before their fling, but it never meant anything it was just a bit of fun. I recently started to develop feelings for him, though, and ended up drunkenly hooking up with him. I didn’t think it was a big deal – my best friend told me she had no feelings for him – but then the other day she told me that she “had, in fact, had feelings for him when they had their fling, but is now over it.” James and I wound up hooking up one more time after that.

Yesterday, though, I found out from another friend that she actually still likes him, and I immediately felt terrible and told my best friend about the first hookup. I couldn’t bring myself to admit that it had happened a second time. She was upset and has asked me to leave her alone for a while.

I have distanced myself from James and nothing will ever happen with him again, but I feel guilty about not being completely honest with my best friend. If I tell her about the second hookup, I risk losing both of my best friends and causing her more pain, but if I don’t, I will continue to feel guilty and definitely lose her if she found out I haven’t been honest. Please help me; I hate myself right now for being such a bad friend and would do anything to go back in time and undo it all.

– Bad Friend