Two of my best friends have had a long-term on-again, off-again fling/relationship. They've both told me things that make it clear they shouldn't be together. I've advised them to end their relationship because they're often unhappy. They called it off a while ago and said they'd try to remain friends.
I also recently ended a relationship, and a few nights ago, my guy friend came over (from the aforementioned couple) to hang out. I used to have a HUGE crush on him – before he and my friend started dating. That night, we talked about our failed relationships and wound up hooking up. We both agreed it was a huge mistake, and we both feel horrible.
Two days later, my girlfriend told me that the two of them are still talking and that she still has feelings for him. That made me feel even worse because I hooked up with a guy she's really into. I plan on telling her – I just don't know how. I always told myself I wasn't the kind of friend who does this, but I did. I don't want this to define what kind of person I am. How do I tell her? And what role can I play in their lives and relationship now?
There's no easy way to tell her – and a lot of people wouldn't. Some commenters on Love Letters might make a great case for you keeping the information to yourself.
But ... you've already made the decision to come clean, so just get it over with, as soon as you're both somewhere comfortable, without an audience. It will be terrible and awkward, but there's no easy way to disclose an upsetting truth. All you can do is tell your friend that your greatest fear is losing her. (Also, you might want to give her ex a heads up; he'll probably want to plan for the release of this information.)
After this gets out, your role in their world might be determined for you. She might not want you around at all, and she'll probably stop coming to you for advice about their turbulent relationship. To be honest, that might be for the best. You wrote of your crush in past tense, but you put it in all caps. Your feelings for him made it too easy for you to turn into a not-so-great friend.
Maybe you need some time away from these people. Space might be best for everyone.
Readers? What do you think?