The Reluctant Cougar

December 17, 2025 by No Comments

Name: Reluctant Cougar |  | Location: Bronx , NY |Question: Your recent email advertising, “Cougar & Boy Toy Speeddating – SOLD OUT FOR MEN” got me to thinking: WHY are younger men so attracted to older women these days?  I am 39 and although I’ve been told that I look “good for my age,” most men routinely guess my age correctly within a couple of years.  (Interestingly enough, most women think that I’m five to twelve years younger, but that’s another story….)  Within the past six months, the guys who have hit on me are between 22 and 32 — even when there are much younger women for them to hit on.  By contrast, the men in their late 30s/early 40s (i.e., the ones who I’m more interested in starting relationships with) seem to be more interested in either cheating on their wives with any age woman or, if they’re single, in women in their 20s or early 30s max.  Courtney Cox’s TV show not withstanding, what do you make of “Generation Y” men’s fascination with Gen X women, Moxie?  And do you have any advice for this very reluctant “Cougar”?  I would much rather be attracting men with whom I could have some sort of long-term relationship and — call me crazy — but I just don’t think the 22 year old fits the bill. |Age: 39

WHY are younger men so attracted to older women these days?

Sex. That’s it. It has nothing to do with a fascination between the generations. The PC explanation is usually that we’re comfortable with ourselves, know what we want, have let go of various insecurities, etc. But the real reason is that they think we’re more sexually experienced and want to takes us for a spin.

It seems to me that the whole Cougar fascination has died out. Ashton has allegedly cheated on Demi, Susan and Tim are kaput. Madonna and Guy Ritchie hit the skids. Even the show Cougartown, which I love love LOVE, changed it’s focus away from the whole older woman sleeping with younger men by the end of its first season. (If you DVR this show, watch the opening credits. Week after week, Cox has them change the sub-heading over the main title to something referring to their horrible judgment in choosing the title for this series and wanting to change it.)

(Interestingly enough, most women think that I’m five to twelve years younger, but that’s another story….)

Mmmm…no…I’m betting they don’t. We all know that women want to be told they look younger than they are, so we usually shave about 5  or more years off our guesses. 35 doesn’t look any different than 39. But 27 looks  a hell of a lot different from 39. It just does. Don’t be ashamed of your age. It is what it is. You’ll fall in to that trap of believing you look younger so you should be able to attract men younger or your age. That’s just a frustrating game of chase your tail.

By contrast, the men in their late 30s/early 40s (i.e., the ones who I’m more interested in starting relationships with) seem to be more interested in either cheating on their wives with any age woman or, if they’re single, in women in their 20s or early 30s max.

Now you’re just trying to justify your desire to go for  a younger guy. You want to take one for a spin? Do it. If you choose correctly and can stay detached, you can probably get a great ego boost from it. Rid yourself of the idea that you’d be dealing with someone who is emotionally mature and self-aware, because you likely won’t be. Guys in their late twenties/early thirties are still figuring themselves out. You don’t want to get caught in that. Also understand that they’re still trying to find their way around the bedroom. My one experience with a much younger guy involved me taking the lead and him following. And while it was good, it was clear he was intimidated by the disparity in our individual levels of experience. He also had no idea what his sexual personality was.  I’d much prefer being with a man with confidence and knew what he liked and what he wanted sexually. That kind of confidence and self-awareness you find in a man our age.

I would much rather be attracting men with whom I could have some sort of long-term relationship and — call me crazy — but I just don’t think the 22 year old fits the bill.

You’re right. A 22 year old probably isn’t going to meet your emotional needs. Or your sexual ones. Neither will the 29 year old. Possibly not even the 35 year olds. You’re 39. The reason, I think, you’re considering this is because you’re feeling frustrated. And that’s what the younger guys see. They assume we’re just beaten enough to be open to their attention. I think it’s the reverse mentality for younger women who go after much older men. They assume these guys have been treated poorly by their ex wives and need an ego boost. This, more than anything, is what I resent about getting hit on by younger men. Rarely do I think it’s based on genuine attraction.

In my mind, neither sex “gets away with it.” I think the older man with the much younger woman looks as ridiculous as the older woman and her younger guy.

Thoughts?

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