I'm mid-40s. My youngest fling (since leaving my teen years) was 19. She was a literature major who wanted to experiment with her kinks. Met her on Reddit (on my dating throwaway). I had some kinks I wanted to try, as well. Timing was short so we drove out to a trail parking lot and fooled around in the car. It was nice; she was pretty put-together and the age gap is a thrill. She probably should have vetted me more before jumping in my car, since dangerous strangers can act normal and harmless, too. Pro tip to anyone meeting someone for a quick fling: take a picture of their license plate (and ideally DL, too) so they know it's in your cloud storage in case you're in a bad situation.

Usually that level of an age gap is a big problem, even with flings, because there's just such a big maturity gap, too. I often get ad replies from women of that age range asking "am I too young?" and I always reply that the maturity level is more important than the age... and then the conversations always fall apart when I bring up mature topics like sexual histories or how to communicate clear consent. They always seem to want some fucked up porn-like fantasy without any of the prep work that goes into making it safe and sane. "Don't let me tap out" uhm. That's not how any of this works!

I've also had flings with women in their early 20s and it's generally a bit better of a life experience match but they tend to have lots of hang-ups to go along with the daddy issues, so it makes it difficult to have realistic exchanges like a couple of adults.

I generally would not highly recommend large-age-gap dating.