I was 26, she was 43 and hot as hell. We were both going through a divorce and spent time comforting one another (carnally).
One day during a seemingly lighhearted converstions she asked, "do you think two people with our age difference could date seriously?" I had not yet learned that women are devious and prefer to give you no warning when asking questions of immense importance.
I did the math in my head and realized that in 7 years she'd be 50 and I'd be 35. I said, "For a few years anyway."
She never went out with me again.