Reminds me of a story I have. My best friend in the military, I set him up with a chick I knew from high school. Petite, flexible, gymnasts. Very pretty girl, she was one of my girlfriends close friends. Anywho, we do a double date (setup), everything goes great, good conversation, good time had by all. We head back to my at the time current girlfriends house, and they have a meeting. Which basically ends up being relayed to me later on that my buddy has a greenlight to initiate physical intimacy. I am thinking by the vibe I was getting from her to him, he could probably take it to third base, with another follow up date he would be in all the way.
So I pull him aside, hand him my keys to my truck, and tell him, "Bro, you are in. If you make a move it will be 100% reciprocated, she is really in to you. Take her home, her parents are out of town, do it now."
He comes back 30 minutes later to my disappointment. I grab the keys from him and say "Tell me you at least kissed her". He shook his head and said he got scared. I said dood, "that was your last shot, I guarantee you she will take that as a rejection. You fucked up". Needless to say, the phone conversations afterwards between the two become pointless and less frequent, he regretted everyday (because he bitched non stop about how stupid he was) for like 2 months.
Moral of the story, be a man, make a move. The worst she can say is no, then you move on with life. Nothing ventured, nothing gained. You cannot go through life like that.
