Two years ago...
I was in my favorite cafe whining about having a birthday soon and getting old. The new, cute, energetic and bouncy (personality, not body) countergirl went on about me not being that old and looking good and it all being a state of mind -- so on.

I was about to teach her a lesson by asking, "oh yeah, would you go out with me then"? But that voice inside my head that usually says things that get me into trouble said, "uh, ask her age first."

That unexpected good advice from my usually bad self struck me as a smart idea, so I raised an eyebrow:

"How old are you anyway"?

"Eighteen."

Christ...

"So, how old do you think I am"?

"About 37, 38..."

What a nice girl -- she actually meant that.

"Allie, I'm turning 45."

"Wow, you're older than my parents"!

Ouch.

I've not let her forget this since, although I suppose it's my fault for not stopping while I was ahead. We're still very good acquaintances, and I set her up with my protege of mine who was only six years older than her.

She threw him over for an older guy, but still a much younger man than myself -- and her parents.
(ChiTown Guy Dating when 35+: sane, single, attractive - pick 2, Fri 8 Jun 2012, 14:58, Reply)