I’ve always enjoyed flirting with women but now that I’m getting on in years, I’m wondering if there’s a point where it just becomes creepy. I don’t want to be creepy but I don’t want to give up flirting either. What’s the cut off or is there one?
I’ve always enjoyed flirting with women but now that I’m getting on in years, I’m wondering if there’s a point where it just becomes creepy. I don’t want to be creepy but I don’t want to give up flirting either. What’s the cut off or is there one?
LemonVibe 
[If you’re flirting with women who are young enough to be your daughter or granddaughter, then it’s creepy. However, if you’re being respectful and the woman is responding positively, what’s the harm?
I’d like to think that when I’m getting on in my years, men (of an appropriate age) will still flirt with me!
[Let’s just call it “35”. If you’re older than that, they can be your daughter, and THAT is creepy enough. Time to settle down, dude. Find someone in your own age bracket and start enjoying the aging process together. It is quite fulfilling!
[As long as the people are of legal age and visibly within at least 10 years of your own age and keep it out of the crude spectrum, you should be fine.
[PG???? Is that you????
[As long as you keep it classy, you won’t be creepy. Women are always much more impressed by gentlemen than the average womanizer. And I’m not just talking about keeping your standard manners – I mean going above and beyond to the point of surprising the woman. Maybe it’s just a Southern thing, but we are so impressed by that.
[If you’re out and out cheesy pick-up lines hitting on someone you should probably stop regardless of your age 😉 Personally, I think there’s a line of appropriateness. I agree with the ‘if she’s old enough to be your daughter.’ But if you’re charming and respectful, a little flirting shouldn’t be seen as creepy.
[In my opinion, creepy is up to you. I know plenty of people who are my age(30) and are creepy. Yet, there are many men much older who can flirt with class and style. Dressing well helps out, speaking intelligently works in your favor and an accent won’t hurt. The most important thing is to take a hint…if the lady isn’t feeling it, cut it out.
[The rule I’ve always heard is, half of your age, plus 7 years.
Then again, just put on a foreign accent and you can say whatever you want, as long as you pick an accent that’s like audible chocolate, like French or Swedish.
[I think what Sabrina said here is key:
“…if you’re being respectful and the woman is responding positively….”
Is she enjoying the attention? Is she smiling and laughing? Is she flirting back?
If so…. sure, go for it. If not… yeah, you’re the creepy old man.
[I think once you get past a certain age, it’s more likely to be endearing than creepy. Just don’t do it in a creepy way—don’t leer, don’t grope, don’t condescend, don’t offer to kill your geriatric wife to marry her. Like others have said, feel the situation out, and if she seems to be reacting in a good way, then keep on getting your flirt on!
[If you’re flirting the right way then the response