When I was let’s see, I have to do some math here 58 I dated a 39-year-old woman for a while. We had a lot of fun playing the “where have you been all my life?” … “in school!” game, but she was already into older men, and apparently she had dated men of my age when she was even younger. So it was no great transition for her; she had already done it. It was a fun trip for me; we used to mess with people while we were out, because they would think that I was an uncle or maybe even her youngish father, and then we’d move into a clench-and-kiss that would disabuse people of that notion. Or maybe not, since we only tended to do that in Alabama.
Much earlier in my life, while I was around 27, I was picked up at a bar by a 42-year-old divorceé and spent a night with her. (I was leaving town the next day, as she already knew, but she only wanted a night and I was at that stage in my life. I’m just sayin’.) That was a fun night for me, and she seemed to have no regrets. Or sleep, that night. Later that year I dated a 35-year-old for most of the summer before I met the woman I would later marry. That was a pretty enjoyable year, all in all. Actually, most of them are, in one way or another.
I’m not actively looking for many 80-year-old women any more, but if the right one came along I’d certainly consider that. Likewise, I’m not about to pass up another 40-year-old, but I do restrain myself, generally, from making the first move there. If she shows interest, then I’ll be actively interested, otherwise just passively so, and from a distance. I may be a creepy old man sometimes, but I don’t want to appear to be so…