Don’t know if we really do it better, raindrop, but we do do it.  Maybe it’s because we do them for both of us and not just for ourselves…

An older, experienced gentleman will remember how lovely curls feel beneath his fingertips, back when nobody in Western Civilization bothered to shave at all.

But if you shave then allow me, gumdrop.  Because an older, experienced gentleman might have been shaving his own sensitive lips since before you were born, mightn’t he?

Hello Mister, would you may be so kind to give me your perspective on how flirts with a significant age gap. Why do you think older man may find e.g. young strong sort haired women attractive?

I’m always surprised when young women worry that older men might not find them attractive.  I mean it makes structural sense, meaning I’m always surprised that any younger woman would be interested in me.  So.  Balance!

But here’s the thing: Before you can be 32 or 52 or… I dunno… 102 you have to have been 22.  And if it makes sense that one liked 22-year-old women when they were 22 then, based on experience and memory if nothing else it makes sense that they’d be just as interested when they’re older.

Meanwhile, it seems odd that women would be attracted to older men because… they’ve never been older.  And… well… how does that even work?  I mean, after my parents divorced my mom dated a succession of men who were considerably older than her, right up into her early 80s when she was as close to a 96-year-old man as I’d ever seen her be close with anyone.  (Maybe age play runs in my family?!?!  Hmm, on my dad’s side my grandfather was 15 or 16 years younger than my grandmother.  Maybe it really does run in my family!!!  But I digress…)  My concern is that at a certain age you just sort of run out of older men.  Or else do the 42-year-old “older men” you were interested in when you were 22 become younger men when you’re 62?


As for your actual question about flirting with an older man you may have to be more direct than you think.  Otherwise, based on my discussion above, he’s very likely to think he’s imagining things.  And no, “more direct” doesn’t mean “hey mister, you want a blowjob!!!”  Because contrary to popular belief that’s more likely to freak out the average older man (or younger one unless he’s very high or very stupid.) 

Yes, that kind of “directness” might panic him even if he’s so infatuated with you his cock weeps salty white across his hands and belly at night while fantasizing about you saying exactly that.  Fantasy ≠ reality.

Instead, by direct you might try engaging him in direct conversation, letting him get to know you (and you him, because it’s still going to be a relationship, right?)  And then perhaps ask him the same question you asked me: “do you think an older man would be attracted to a strong, short-haired woman?”

The very good thing about that particular question, by the way, is that you have a graceful “out” if he says “goodness no, I’ve always been into women who are older than me.”

Best of luck whatever you choose to do!  Good question and good food for thought.  Thank you for asking.