40 for sure. 30s pushing it.

If she's 21, I don't think his AGE is what constitutes creepiness, but more his manner. Does he act aggressive, will he not take no for an answer, does he otherwise cling or stalk her?

Well I'm 53 - and sure as hell all the 21-year-old girls I hit on think I'm as creepy as fuck!

I don't do just because we have nothing in common to relate to. 21 year olds seems like children to me... simply put... too much of generation gap.... been looking like that for many, many years. I can't see anyone in their 40's!!!! ...and then again... maturity level and complimentary factors could lead to possibility but it will be the exception and not the rule and not expected to last. Expectations on the relationship from both individuals. the 21 year old may end up being the creepy one. What is the motivation in both sides? Can of Worms Alert!!!! I like good good conversation after love or sex. flow of ideas between equals.

If you get parental consent, it doesn't matter.

Roy Moore

In my opinion, the said man must be at least 5. Actually, age doesn't enter into it. What is most relevant is the WAY IN WHICH THE FLIRTING MANIFESTS. About half the time, in my antique experience, there is violent unconscious intent informing what the man says and informing his body language during the flirt. Hence the phrase "hit on": to hit is to commit violence.

When they have kids within ten yrs of the victim, i mean the younger woman you have eyes for

I think it is odd when they can be your own daughter...you have to ask to meet their mother, not out of respect, but to make sure you didn't date her. I did the punk rock up until I was about 38 or so, saw a lot of people who were dating at half their age or so.

There is a world of difference between hitting on someone and flirting. I know a number of octogenarian flirts both male and female I don't find anything creepy about any of them.
Why does age matter? I have seen some creepy 21 year olds hitting on women their own age.

I can't answer for age but I nuts conversation would be disturbing what would be the commonality in the maturity of the conversation. I can see what the cartoon artist from playboy would make of that the girl would have $ signs and the guy steam coming out of his underwear thinking only of physical attraction.

I am old, I am not, yet, dead.

I won't 'hit on' someone I think is too young. I have not been able to have kids, yet. I do hope to do so some day. Based on what I have read and experienced, I think that asking a woman my age to have kids is asking a bit much. In short, in dating I feel like the proverbial old man searching for a trophy wife or 'perv' experience... I am NOT. That is NOT what I want. I just want the normal "grow up, get married, have kiids" experience but... I am late with one (my wife and I tried, she passed away after an 8 year battle with breast cancer).

So, all that said, I restrict my active searches to women 35-45 and feel creepy about 35 year olds who respond. I actively search for about a 15 year gap (or less) meaning that I really am looking at 39 year olds.

Now, ALL of that said, if I happen to meet someone, and she doesn't have her current age tattooed on her forehead (or elsewhere) and we are having a great time and we decide to, give a 'deeper' relationship a whirl... I'd have a conversation with her before we took that step but I am not opposed (really no longer opposed, I was when I was young), to the thought of a gap in years... IF, it's a big if, the two are well matched, in spite of said gap in years.

And by 'well matched' I do NOT mean one has a lot of money, and the other a lot of naivete. I mean that they just click on a lot of levels.

I have met gals my age, or higher, who are NOT compatible. Either because they aren't ready to have a deep conversation, or because I am not physically attracted to them (or vice versa, and before your thoughts to too far in this direction, i have met some women who are smokin' hot even as far up as 70!), or... and this one is weird but it is there... culturally compatible.

Now, strangely, I have met two girls so far who are just 'old souls.' They spoke MY language, liked the same things I like. I could talk to them as a friend and NOT feel like I was a father or grandfather talking to them (I mean cultural compatibility where we truly speak the same language, despite the years). I did not 'hit on' either. One of them was old enough, mature enough really, that I made my feelings clear, and by that I mean I said I would be open to exploring the possibility. She never did answer, but she never left my life either and no, we never became a couple. We are just good friends. We respect each other and have deep feelings for each other. I think at this point we will never cross into the romantic realm though, and I am ok with that.

So, in my book it is weird to 'hit on' someone when you do NOT know them well enough to know if they are the least interested in you, or that you are more than interested at a surface (probably lust) level. It is up to both of you to determine if the number of years is a problem. You both have to talk openly and honestly about that. The thing is, that communication needs to be there even if there is NO gap in ages.

Total Honesty? From this front, here we go. I am 68 years old, and am a part time college student, so I am not run of the mill, but I do spend some time time with younger students, and frankly, I do enjoy the company of the coeds. I do not expect or seek sexual favors, but enjoy a young and fresh look at life.

The formula is half the man's age, plus 7. So to date a 21 year old, you should be no more than 30.

Somewhere between 31 and 36. I picked 31 because at that age (hers) the 10-year differential creates a substantial difference in life stage and experience. I picked 36 because at that age (his) he literally could be her father. I made a range because some 21-year-old women can be especially mature for their age, so she might actually prefer flirting with an older man. I don't like setting anything too firm, but, yeah, somewhere in there is where it starts feeling uncomfortable.

I don't have any daughters. If I did, I'd probably set the bar lower, but this is me without an emotional involvement in the question.

Consenting adults, blah blah blah, not my place to judge. But, speaking for myself I'd be disinclined to flirt with a woman so young. I can't imagine we'd have much in common, and perspectives are vastly different the further apart the ages are, especially at such a young age (more wiggle room as people get older). I might have considered 21 compatible when I was 30-ish, but I'm not sure. At 40, I'd maybe consider 30 — but I'm talking hypothetically, and each individual in reality would deserve to be considered on their own merits.

Tough question, considering both parties are most definitely adults. In a way, I feel like age is just a number so long as adults are involved. That said, as a 45 year old, I know that I would have little to nothing in common with a 21 year old woman. Could I find one attractive? Absolutely! Might I flirt with one? Probably not intentionally but I am a poor judge of age sometimes and I might think she were closer to 30.

Right or wrong, men are visual people and any man who tells you that a young woman (~21) could not be attractive is lying to you. Generally speaking, most men no matter what their age would find a 21 year old woman attractive. Maybe it's just because I'm not the overly aggressive type, but I think most flirting is harmless. A 60 year old flirting with a 21 year old would be pathetic for sure. Probably a little creepy too, but that's mostly for the target of the flirting to decide.

If he is a man of God then any age is unacceptable to hit on a 21-year-old woman. Creepy Bible thumping jerk (:

Old enough to be the parent.