I said a couple of things that hurt a friend of mine who's been giving me indicators of interest, such as heavily flirting, being touchy feely, sitting on my lap, etc. I hadn't tried anything because she's married. I knew they were having problems though, because at her bday party she didn't even talk to her husband the whole night and it really bugged me because I like the guy. Well, the guy's actually a pompous ass, but I try to be the better man... She and I were out to eat with friends one night where we were talking about relationships and how best friends make terrible couples because my ex and I were best friends. At this point I knew her relationship was on the rocks but I still said "Laura, you guys were best friends right? So I guess it can work". Part of me wanted to fish for information and the other part was trying to give her positive reinforcement, but I could tell that what I said had stung her. Oops. A week after that we went out again and this time she fessed up that they had gotten divorced and it was final...this was why we went out, to celebrate. I confessed that I knew all along that there was trouble. And I stupidly brought up what I had said the week before and apologized about it because I had been feeling so guilty all week. She laughed but acted surprised and threw her sword (from her drink) at me. I should never have brought that up! Later as we were helping her stealthily move out, while moving some equipment we scratched the finished railing, to which I said "that'll buff right out! ....sorry" I blame the 3 cocktails I had up till that point. She got upset, went into her room to talk to her friend alone, actually cried and asked her friend "why would he say something like that?" After we were done moving her stuff I gave her a kiss on the cheek, in my mind as an apology and she said "omg he kissed me!" (I hadn't been very affectionate or touchy feely up till that point) But since then she has been distant and has gotten a new bf.