How long is too long?

So for about 2 1/2 years now, I've sort of had this crush on a guy. We have tons in common and everyone (including our teachers) used to assume that we were dating, but we were "just friends" at the time. For two years, he has been in a relationship with a friend of mine. She was talking marriage, even when she was in high school, so it was pretty serious. She treated him like crap, but he didn't seem to mind.

They broke up about two weeks ago. I'm kind of conflicted. I purposely limited my contact with him while they were dating out of respect for her. She has been talking to me and asking for advice about how to cope and whether to try to get him back, so I try to be objective, but I can't help but get jealous and feel like I'm betraying her trust by doing so. We have never been very close friends, but I try to respect her.

I didn't ask him out before they started dating because I was afraid and shy, but I'm terrified that if I wait too long again, I will never get the chance to because we are now both seniors in high school, looking to go to college out of state.

We have been talking and hanging out constantly since the breakup. The question is, how do I know when it's OK to try to start something? Should I let him make the first move? I don't want to be a rebound, but I don't want my last opportunity to be stolen away by someone who acted faster than me again. How long do I wait?


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  • Let him get over her first, be a good friend and be there for him. But after that long, he will only be wishing he was with her. Don't trash talk your friend[he won't appreciate that since hell still care about her], just says that's too bad and I'm sorry I wish things were different but always remember I care about you and I'm here for you. Just be his friend till you think he's ready to start getting back out there :)