It's just a bit on the creepy side now when you're 37. You can probably even hold on to it well into your 40's. When you're seriously middle aged and beyond though, you'll really be looked at as a sick freak.
I'm 41, and I find the idea of relations with a 23 year old to be totally repugnant. Then again, my step-daughter who I raised from the time she was 12, is 26, so that probably has a lot to do with it.
I agree with you. I benefit a bit from looking younger than I am - people tend to figure me for late 20s or so. I benefit also from genetics (I have all of my hair, and more), my macho good looks (of course), as well as never drinking or smoking in my life (though I enjoy a good cigar maybe 12-15x a year these days). I was never a big boozer, partier, etc, and that does make a difference in looks to an extent.
Also when it comes to women, in the age group that I like and even more so with older ones, a lot of the seduction game has to do with having a very good rap and distuinguishing yourself from other males out there. I do both easily, so having a lady companion has never been a problem for me in my adult life.
I date a woman in her early 30s who is very goodlooking: she is a musician and shuttles a lot between LA and NYC. We speak daily and see each other for a long weekend every 3 to 4 weeks. That suits me just fine. I agree that I naturally feel more comfortable with her (a 5 year spread in ages) than I would with a girl who was 23 or 24. But its negligible - if a woman is mature and has her act together, it tends to not matter to me very much that I'm older.
I don't date women close to my age nor older, sorry. ;-)
Don't sell yourself short. I feel the same way, and we have no children yet.
I prefer to think of it as wisdom from experience. As I told my wife of twenty years recently, "they look like children with big racks to me."
After the honeymoon, mine was damn near intolerable until she hit her mid-thirties. Who wants that again?