There were more mistakes than that. But there was also no compromise. It was pretty quickly "I'm not going to listen to that shit" when Boston, Kansas, Journey or something I liked came on and the radio turned to Alan Jackson or something else equally shit-tastic. No negotiation. Just raw fury if there was any effort on my part to find some middle ground. She's been angry all her life and I could never change it. I tried, though, but the more I tried the worse it seemed to get. Her way or the highway. Fuck what anybody else wants.
I'm scarred from it. Seriously. It changed my personality.
So... how do you approach that transition from best friend to something else? What's the awkward scale there?
That wasn't intended as a slam on you, believe it or not. I'm sure at first you accommodated just to be nice, or keep the peace, whatever, and then she came to expect it. Road to hell and good intentions and all that. You sound as relieved to be out of that relationship as I was when my divorce papers were signed. Good for you.
The best friend transition came after a fancy company Christmas party his company threw at a local country club. We were dressed up, had a nice evening, great food and wine, dancing... And at my door, he asked for a kiss good night, totally out of the blue. I was surprised enough to agree before I remembered we were just friends, and his kiss was just a simple peck on the lips before he ran like a scalded dog. Not so much that if it were unwelcomed, it could be awkward, but just enough to pique my interest and give me something to think about. He waited until NYE to try again, and then I kissed him back. Waited a bit longer to get horizontal just to make sure. Sparks flew. Engaged six months later.
I'd try the subtle, simple kiss-and-run and see what happens. No sparks? No harm, no foul. Sparks? Give it another try later and go from there. Don't go for the gusto and get nekkid until you are sure it's the right thing to do. You really can't unring that bell.