It can seem creepy but in the realm of things, it just doesn't matter. If both parties are consenting adults, it would be up to them. Some people find some older people sexy. How many 21 year olds would love Curt Russel to hit on them or maybe Sam Elliott? Some older guys may be sexy to some younger girls. I know a lot of younger girls look sexy to me but I would only hint at hitting on them unless they appeared interested. It don't have to be a lifetime commitment type thing. Sometimes a memory of a lifetime can come from a chance meeting of some guy you thought at first was a creepy old pervert. Now you can be satisfied in the fact you were right. I feel young at heart but I still probably wouldn't hit on a woman under 40. Now when they hit on you, it's a different story. She's probably a hooker.

It all depends on the amount of money in his bank account.

I have been in relationships with women 3 decades younger than me. Its hard there are the stares the people thinking they were my daughters. The hardest part is no shared experiences music films books are all how I measure my life. An example of this is protest or folk music it was part of my life and will continue to be until the flying spaghetti monster comes for me. For them its old people music.

The rule is half your age plus seven, so anything out of that range is super creepy.

Don't date anyone younger than your own children.

my guess 55 as then there is not a chance in hell of anything on the cards so why bother someone who has her youth to enjoy

The "half the man's age, plus 7" formula already given isn't bad, but others may have a different opinion.

I used to think +/-4 was ideal under the idea of “in high school at the same time” rule. Then I met this woman and developed a ridiculous crush on her. She loved music that came out about a decade before I was born and popped out her first kid years before I was ready to have kids. She was also further in her career than me and living well. She’s also 8 years younger than me and I now subscribe to “old enough to go to a bar” and commonality.

In my vocabulary, flirting and 'hitting on' are two entirely different things. There is no age limit on flirting. If it's creepy, it isn't flirting. If it's creepy, it may have been meant to be flirting but was delivered clumsily. Flirting is a good natured compliment of one's sexuality.

I really think it depends on the maturity-levels of the people involved.

My ex-wife and I married when she was 19 and I was 29. Due to her mom's teenage pregnancy, her mom was 37 at the time. The thing is that my ex and I had a lot in common (e.g., neither of us ever partied, we were interested in academic pursuits, we were similar in politics and religion). I never had anything in common with her mother despite us being closer in age. Her mom likes to party to this very day (despite being in her 50's). My ex and I were together nearly 12 years so there is evidence that it can work. Interestingly, whereas I was nearly 10 years older than her, her boyfriend after me was nearly 20 years older than her (and two years older than her mother).

It can work under the right circumstances, but those circumstances are rare. I wouldn't discriminate against someone in their early 20's, but I have a soft limit of 25.

Lastly, I don't generally, knowingly, and actively, pursue people under 25, but I am willing to go out with someone that young who pursued me.

anyone above 25 M/F are adult enough to determine who they date. I would say 21 is not that fully matured. but past 25 he be could 25 and the women could be 60 or vise versa as long as it is a consenstial

When my daughter was a teenager, she worked as a check out clerk at a grocery store. She used to tell me about these "old men" who would flirt with her at the check out. I asked her how old these old men were, and she got a look on her face like she was trying to calculate their ages, so I said "my age?" And says "yes!". I was around 46 at the time.

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?

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

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.

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