Alright, I not-too-recently broke up with my girlfriend of a year and a half, and have since been enjoying the single life. Ya know, getting drunk at parties, making out with beautiful girls for the hell of it, making an ass of myself in my intoxicated state and passing out on a pile of coats... OK, all but the making out only happened once...
Anyways! Last night I was hanging out with my friend Brittany, who also happens to be my friend Nick's ex... This is pretty normal, other than that I realized last night, while laying on the couch with her, arguing over who gets the good blanket, that I have feelings for her. Yes, she is my best friend's ex, and yes, they still frequently hang out, but no, I don't foresee them getting back together. He wants it, but she broke up with him, and she DEFINITELY wore the pants in their relationship. He has asked me not to date her, unless she started showing interest in a guy named Sears, a real asshole womanizer with a big ego, a '74 Toranado, and, from what I've heard, a bigger 'drive shaft' than his car. He's moving in with her soon, and that could lead to what we're trying to keep her from. Nick loves Brittany, and I have some strong feeling for her, which have been growing for years, so we don't want her to go through the shit he's been known to start.
I know I have to tell Nick how I'm feeling about her, and I know I have to tell her, but my question is: do I tell Brittany and start the courtship process, risk angering Nick by not telling him right away, and possibly saving Brittany from Sears (if at all possible) or do I tell him first, and risk wasting time while he mulls things over and tries to get her back, then (basically) gives me permission to date her. The second option is dangerous, because if Nick tries to get her back, and that falls through (which is likely) she may run to Mr. I'm-well-hung-and-you-like-my-car-and-I-live-with-you!