Younger Men and Older Women

A couple of weeks ago while I visiting Southern California, my ex-girlfriend there told me the story of some colleagues of hers. One was a tall, slender, elegantly beautiful, but slightly older-looking woman over whom everyone in the office took much interest, but who rather kept to herself and was none too talkative about her background. The other was a mid-20ish player kind of guy who was constantly chatting up all the cute girls in the office and regaling his coworkers with tales of his conquests.

The 20-something player frequently made small talk with the beautiful, elegant woman in the office, and tried to make some headway with her, though he never could. Then, one night out at the bar for a happy hour, in a group discussion, the elegant woman happened to mention her age, perhaps emboldened by alcohol: she was 50. According to my ex, she looked so good she could easily pass for early- to mid-30s, and that’s probably what everyone assumed she was until she said it.

Upon hearing her age, the player guy who’d previously been so interested in her recoiled with horror: “Oh my God,” he said, “you’re fifty? Don’t you think you should tell people that? Oh my God.”

You can imagine how this gal must’ve felt. None too good, I’d wager. This is just one of the reasons why older women – even those only a few years older – so often get weird around younger men.

Older Women’s Reservations About Younger Men

There are scores of reasons why older women act strange with younger men, or shut those younger men expressing interest in them down. Some women are more sensitive to age differences than others; the more hedonistic older women I know and have consorted with (I’ve had a few women in their mid-30s) don’t much care for age, really, beyond a few passing concerns. Other women may freak out because they’re a month older than you. It’s very much dependent on the woman.

But universally, as a woman gets older, she tends to get a lot of bad reactions – like the one in the tale above – from younger men, and it creates a bit of a wall for her between her own feelings and her ability to let herself become interested and attracted to these younger men. She begins viewing younger men as unattainable, and that means she starts resenting them and disliking them.

This ties back to evolutionary theory – women are inclined to seek out older men who are likely to be more established financially, socially, and otherwise, and be better able to provide for their young, while men are compelled to seek out younger women, who have more time left on their biological clock to provide more sons and daughters to their mate and are more likely to get pregnant more easily and have fewer complications from childbirth.

But when it comes to men, we don’t actually seek out youth itself, per se, but rather a youthful appearance – which means you might run into a 19 year old with an old face and find her not especially of interest, and you might run into a 31 year old with a youthful face and find her beautiful. So you might not always be inclined to stick to this paradigm.

But, while there often is a bit of an intrinsic evolutionary disadvantage with this kind of mate selection, it’s usually more on the man’s side than the woman’s. The reservations women tend to have come more from nurture than nature; they react negatively against younger men because they’re accustomed to younger men reacting negatively against them, and/or being immature. Which should hearten you; whenever you run into issues that stem from someone being acclimated to expect something from other people, you know that all you need to do is show you’re different, and you oftentimes get a different response.

Note I said show you’re different, as opposed to say you’re different. Most men try to say they’re different, but women put little stock in men’s words. You need to get the right subcommunication down about age; that’s the hard part about disarming the age question.

Before we go into that though, let’s spool through the main reasons older women tend not to treat younger men so favorably:

  • Immaturity. Many younger men are immature. While that cute 27 year old you’ve just met used to go to all the wild parties and get loose a few years back, she’s at a point now where she’s moved beyond that and these days prefers some good conversation and a man who can turn her on without screaming his head off or taking her to a frat party with sticky floors and a couple of beer pong tables. Unfortunately, most of the younger guys older girls meet don’t realize this, and keep trying to do the same things with them that they do with 20 and 21 year old girls, and the older women come to expect this behavior from younger men and avoid them because of it.
  • Lack of Life Experience. I had to learn the hard way not to talk too much about myself or my fascinating life with younger women because they simply couldn’t relate to it. Fact is that younger people really don’t have much life experience, which makes for less stimulating interactions for older, more worldly paramours. Older women know this, and prefer to stick to older men who can more often relate to them better.
  • Lack of Sexual Experience. Younger men simply don’t tend to be as sexually experienced as older men. They don’t know as well how to please a woman; they don’t know as well what women want in bed; they don’t know as well how to get a girl excited for intimacy. Most older women are none too interested in taking the role of teacher to young men – they’ve already been there, done that. Now, they just want a guy who knows how to satisfy them, and they know they’re more likely to find that with an older man.
  • Rejection. Quite possibly the biggest one, many older women fear rejection, disgust, and mistreatment by callous younger men, who tend to be both less sensitive to women’s feelings (as they’re less socially calibrated than older men) and more judgmental against older women (as they’re accustomed to the artificial environment of school, where they’re constantly surrounded by women of their own age with no more than a year or two of difference). Women will quite often go immediately into auto-rejection upon finding out a man is younger than they are, simply to protect themselves from being hurt.

Those are the big ones. Immaturity, lack of life and sexual experience, and rejection – the thing an older woman fears getting with a younger man. Those are the things you’re going to be targeting overcoming when you go for older women.

The thing is, all these are easily surmountable if you do a good job showing you’re different. Women know there are younger men who are mature. Women know there are younger men with life experience. Women know there are younger men who know their ways around a woman’s body. Women know there are younger men who like them and appreciate them and won’t reject them. You just need to show these women you’re one of those men.

Telling Women You’re Older

I remember when I was fresh out of college and had just begun my new job in Washington, DC in mid-2006. I kept running into problems where I’d have things going swimmingly with a girl, she’d be very interested in me, and then she’d ask me my age, I’d tell her, and she’d shut down. This culminated for me with a girl I met on the metro.

One night I was riding on the train, and I started talking to a really cute blonde. She was very much into me, asking me all kinds of questions about myself, and I was starting to get a really good feeling about things. Then she asked me my age.

“I’m 23,” I said. She looked stunned.

“Oh,” she said. She paused a moment. “Oh,” she said again. “I’m 27.” Then she turned away from me and got really quiet.

I was sitting there, mildly shocked, thinking to myself, “What? It’s four years’ difference – who cares??” I tried talking to her again but she just acted weird. She told me she didn’t date younger men, she’d tried it and it just didn’t work. When we reached her station, she seemed to calm down a little, and almost seemed sorry for her weirdness and for acting that way. Maybe she’d started having second thoughts, but by then it was too late, and she left without giving me a way to stay in touch with her.

It was such a clear example to me of how powerfully age can shut down an otherwise excellent interaction that I made it a point then and there to solve the age thing. My first approach? Lying about my age.

Now, I’m a very pro-honesty kind of guy. I truly, truly believe the old “Honesty’s the Best Policy” line, and I’m a firm believer that lying is the dominion of the cowards and weak men too afraid to stand in the world and be judged for whom they are.

But when it comes to age, I think it’s okay to make some exceptions. This is where, “It’s not lying; it’s flirting,” comes into play.

Reason why is because age, for many people, is such a bright, blinding light of a problem that it crowds out everything else important and gets used as some kind of artificial metric of worthiness. Rather than being judged as a person, you get judged by a number. But I am not my age. And neither are you. I’m just me, and you’re just you. So in this instance, the only one I can think of offhand, I think it’s okay to flat out lie – especially if it’s because you’re very young.

So, I started telling girls I was older. Personality-wise, I seemed and acted more mature, so it wasn’t hard to pass for older. And besides, age is the kind of thing that gets mentioned once, and never again. Women are just checking to make sure you’re not one of those dreaded “too young” or “too old” guys, and then you’re fine. Men do the same thing to women.

Is lying about your age problematic if you want a long-term relationship? Possibly, but it’s not a death sentence provided you clear things up soon after bedding a girl. Is it problematic if you want a one-night stand? Not at all. In fact, she never needs to know. There are plenty of other things she’ll never know about you and you’ll never know about her, so your actual chronological age shouldn’t seem like such an important detail for a woman you’ll spend one night with and never see again.

What I started doing with women after that was, when they’d ask me my age, I’d ask them to guess. And then, because I found that women always guessed an age close to their own, I told them they were close, and then went a year over. So it’d go like this:

Girl: How old are you?

Me: What do you think? Take a guess.

Girl: You’re… oh, I don’t know. Just tell me.

Me: Just guess. It isn’t that hard. Pick a number.

Girl: 24.

Me: Close! I’m 25.

The reason I recommend going a year over is twofold:

  1. It seems more real – you’re not just agreeing with what she said; you’re correcting her, and
  2. It gives you a little bit of an age boost over what she thinks you are – being a little older never hurts when it comes to wooing women.

The reason I don’t recommend going more than a year over her guess is because you risk not being believed. If you’re 22, and some girl guesses you’re 24, and you tell her you’re 28, she may just call your bluff.

My first same-night lay from a nightclub happened soon after I implemented this approach to discussing my age, and the girl’s and my initial conversation went like this:

Me: Oh no, you look so bored :(

Girl: I’m just relaxing and watching the dance floor. My friend is out there dancing with some girl.

Me: Ah, well, good to chill sometimes and take a break from the craziness.

Girl: How old are you?

Me: What do you think?

Girl: Um… 25?

Me: Not bad. I’m 26.

Girl: Oh, thank God! I keep meeting all these guys who are 23. I’m 26.

A few hours later we went back to my apartment, took a shower together, and went to bed. Probably wouldn’t have happened had I told her I was 23. I saw the girl a few times, and even tried to tell her at one point I was actually 23, at which point she freaked out a little bit and said, “No. No way. You’re 26. Right? You’re just kidding. You’re not 23.”

To which I said, “Yeah, you’re right. Just kidding you. I’m 26.” Figured it was easier just to let her believe it than shock her with my real age. I wasn’t planning a family with her or anything.

Disarming the Age Question Without Lying

The age problem still bugged me, and since I don’t like lying I wanted to find a solution that would allow me to be honest but still get the girl regardless.

I asked two of the guys I trained under in early 2007 for their approach to dealing with the age question, and they each had very good, and very different suggestions.

BradP helped me craft a specific response to older women’s objections. It was, “You know, I meet a lot of younger girls, and they really are at the peak of their beauty and have the best bodies out there, but I don’t know, beyond maybe an hour or so of conversation, they just can’t hold my attention.”

The first time I used this, the girl, who’d immediately prior to its use been about to auto-reject, began agreeing heartily with me and telling me how younger girls were so inexperienced and didn’t know anything about the world. If I remember right, I took that girl home later, though the four years since have somewhat clouded my memory.

Sebastian Drake took a different approach to this when I asked him. He said, “You know what I’m doing now? I ask women the age question first. It takes the ball out of their court and puts it in yours, so that you’re screening them on age instead of them screening you on age. I ask it almost right away after I start talking to girls these days.”

So I started doing this, and it worked extraordinarily well too.

Both of these things are these days, four years later, still ingrained in my approach to dealing with age. Per Sebastian, I ask women their age first about 75% of the time these days. Not always at the outset of the interaction, but at some point I usually ask. Brad’s response to women auto-rejecting on age I use when I get objections like, “Oh, you’re young.” I’ve modified it a bit, and I don’t always say exactly the same thing, but it still works great.

At some point I added another piece of my own that works well with my style: I make a little quip about a girl being old, then move the conversation on. The delivery is very similar to how I deliver chase frames; make the comment quick, with a wry smile and a seductive look, so it’s both sexy and so she know I’m only ribbing her, and then immediately change topics.

The line I usually use is, “You’re almost ready to retire then, right?” but I’ll also say whatever springs to mind, like, “That means you’ve got your rocking chair and ten cats at home, yeah?” or something along those lines. Verbally, it looks like this:

Me: How old are you?

Girl: Uh… I’m 33.

Me: My God. That means you’re collecting Social Security now, right?

Girl: Haha. How old are you?

Me: I’m 28. How long have you been living in town here?

And then age is dealt with. If necessary, I’ll use Brad’s disarming statement, but it usually isn’t called for. Partially that’s because it gets easier once you’re over 25 or 26 or so; once you hit 27, age is virtually a non-factor. But a lot of that’s because once you have your nonverbals down, and you disarm age by asking about if first (if possible) and using a quick little quip that shows you don’t really care, then immediately moving on, girls realize you aren’t going to make a big deal about age, and tend to respond in kind.

My process for age, then, looks like this these days:

  • Ask girl first. Not a big deal if she asks me first, but I’ll take the reins if I can, and especially if I can tell she’s skirting the issue and is afraid it might be a big deal. I want to get it out of the way rather than hanging over her head making her nervous so she can start getting comfortable with me and opening up to me.
  • Make a quick, funny quip and move on. Make sure you practice your delivery, and change the topic with speed and social fluidity. This has to be done right or it might seem insulting. You want to put her at ease, not raise her hackles.
  • Lightly pan younger women if she makes it an issue. “You know, younger women I find don’t have a whole lot to talk about. I don’t know if it’s life experience or what it is, but I don’t find them terribly interesting. Great bodies, yeah, but not all that worldly.” Something like that. Don’t be mean to younger women – you don’t want to seem like the bitter guy who can’t get young girls – but just be matter-of-fact about it. It gets older women feeling more comfortable with you and gives them something to agree with you about in an “us vs. them” kind of way. Women always want to believe they’re superior to the competition, so when you help an older gal recognize ways she’s better than the younger gals she sees so many men pursuing, she loves you for it.

Play around with these. If you’re 23 or younger, you may need to just lie about your age, because aside from fear of rejection many women may just be biased against you for being too young. Just have them guess your age, and then go a year over what they say.

Ultimately, age is just a number and shouldn’t have the kind of “certain death” impact on your seductions that it has for many men. Follow these steps, then, and it won’t – and you can enjoy bedding cute women a few years your senior instead of being restricted only to younger gals and girls your own age. Flexibility in your dating life is something you should definitely concentrate on having; this one’s worth spending a couple of minutes correcting.


Chase AmanteAbout the Author: Chase Amante

Chase woke up one day in 2004 tired of being alone. So, he set to work and read every book he could find, studied every teacher he could meet, and talked to every girl he could talk to to figure out dating. After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website. He will teach you everything he knows about girls in one single program in his Mastery Package.


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Downdiggity's picture

Hey Chase. I've been running into this problem a lot lately (I'm 23), and thought I ought to see how Chase handles it. And great to see, you have an article about it!

I'm excited to try this out. There was this girl I met a week ago, went out with once, and could tell we were connecting and she was interested. Then I ran into her tonight, and she said 'if only you were five years older, or I were five years younger...'. She was clearly interested, giving me doe eyes, but wasn't comfortable enough. Now I know, I should have given her a funny quip there, and/or lightly panned younger women.

Until next time!

Anonymous's picture

Well, you are wrong. I'm 52, look great, and younger men ask me out all the time. I'm the one who says I"m too old for them, they dont believe I"m 52 and they dont care about the age. And im talking about really handsome guys in their 30s or younger, model type, with beautiful faces and bodies. So I don't believe a young guy would be repulsed by a beautiful woman in their 40s or 50s.

Anonymous's picture

Sounds then, as though your comment of being "too old" for them, is baseless, and (like he said) youre too caught up on numbers, because society says u "look weird" by dating younger men. Otherwise youre just validating his point.

Derrick's picture

This seems useful for the guys who are just starting off who want to try and gain some experience with women, figuring in many cases that going for a girl who is a bit older (and thus not being as actively competed for) is a good idea, only to find it's still a pain in the back.

BladeRunner's picture

... And what happens when you're for example 35, and target 19 years old girls?

Girls of that age seem to be quite sensitive about the subject, and, in clubs, tend to reject you for it right away. (many times they just look at you scared or repulsed to begin with)

Anonymous's picture

Stumbled upon this article and was very impress. I’m 30 year old woman an I am still getting use to dating only men in their 20’s. It’s not that I won’t date men in their 30’s it’s more that they won’t date me. The one’s I know have politely rejected me when I asked or are already dating (or want to date) a much younger woman. Men in their 20’s tend to be better looking, better dressers, and love it when a woman asks them out. I am sometimes amazed at how amazed they are by my confidence and strait forwardness.

I love this article because it really hits the key issues as why women are afraid of dating younger. It doesn’t bring up superficial issues like money or the ability to provide for a family. Other articles of this nature tend to bring those topics up as if most women only care about money and popping out children. Thank you for writing this.

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