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.

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 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.

Is Roy Moore at it again?????

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

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

@AMGT - We are dealing with something that cannot be relegated to numbers. We need to look at motive. As an example with which I have personal experience, my wife is 15 years my junior. We have been together for what could be considered forever based on current trends, and we have four really cool children, even if one is a religious nutcase.

Motive, folks. Motive.

I think it would depend on the girl and the circumstances. There are a very few girls who are attracted to older men. Some girls, as well as some guys, look for older men (sugar daddies) to support them.

When I came otu as a gay man at age 23, I looked young for my age and was often mistakenly thought to be still in high school. There were several times where gusy who were older than 40,hit on me. I guess they were hoping I was naive as i looked. I found that to be creepy.

Generally, I adopted the" ten year rule." I would not date anyone who was mor ethan 10 years older than I was. This was mostly because as the age difference gets bigger, there is less chance of there beign anything you will have in common,or enough in common to make a relationship worth pursuing.

I wouldn't say creepy. Creeps can be any age (or gender). But it's just weird, or something. 21 is just coming into adulthood. A person that age could benefit from having older friends, but their dating us better off near their own age.
But please consider that no one wears their age pinned to their shirt. A guy can't know what he's doing until he finds out. Some women look older than they are, and some much much younger. There is no smooth way to ask.

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

Whenever I see a large age gap in a relationship, my first thought is "when X was born, the other person was X." If I was 10 years old and you were a baby...we were both kids, and maybe it's ok. But if I could have been old enough to have you as a child myself...that's creepy. Sexual attraction is one thing. I'm 47 years old and I find many young women very attractive and I can reminisce from afar about how I USED to be in my twenties and what it would have been like to have a relationship with an attractive twenty something, when I was a twenty something. But to actually act upon that impulse? No way. The other thing I don't get about older men hitting on younger girls. -- the older I get the younger everyone looks to me. Unless they are a glamoured up Victoria secret model (and even sometimes then) they look like high school girls. I am seeing 20 to 30 year olds that look like college kids. That's just creepy. I am sure there are exceptions, but I believe we all just need to stay in our own lane. My wife and I are 3 years apart, she's older. We have a lot in common, but still 3 years for memories in high school- events, music, etc. were different. I don't know how people with huge age spans even have a conversation. What could they have in common beyond sex? I just don't get it.

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.

I wonder why you made this post.... hahaha

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

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.

I don't really hit on women at all. Especially with this 'me too' movement going on, it seems like every woman is at the ready to judge me a creep at any second. I know that's probably not true, but there's more to it than just that. (I hear women tell stories about getting hit on at place X and how they just want to get their shit done.) Now, if some young gorgeous woman thought I was brilliant and wanted to hook up with me (which is never going to happen, but for the sake of argument) I don't think there's any way I could turn that down. But I don't know that a relationship would work (that's ignoring the fact that I doubt I'm going to find anyone I'm compatible with, let alone a beautiful intelligent woman who doesn't want kids who also happens to be a decade and a half my junior.)
But basically I'm just in the mode where I hope I strike up a real conversation with a woman without having to be the annoying guy who hits on everyone, genuinely find her interesting, and make her fall for me with my biting wit and unbelievable charm that I, for some reason, never display publicly.

I thought it didn’t matter. But then I saw some 35-40 something chasing 20 from a different perspective, so maybe I was wrong.

I went out with a 22 year old when I was in my mid thirties, and found out we had absolutely nothing in common. My only attraction to her was her beauty and her sparkling personality. Since then I only dated women who were within 4 or 5 years of my age. I think for most people that woul be a good rule of thumb.