How to pickup 30-40 years old women as a younger guy?

[Bokanovsky]

We then exchanged numbers. She ended up coming to my place a few days later (but had a male friend accompany her)

While at my place, she compared me to Jeffrey Dahmer. Needless to say, we didn't progress any further.

I think I'm starting to understand your stylistic inspiration:

 

[SW15]

You have to know you target audience. You are not going to do well with women in the 30-35 range. Those women are typically in their "last call" stage and are looking for a man in his 30's or 40's to start a family with ASAP. They are not going to treat you as a serious candidate.

This is true. There are occasionally women pushing 40 who are still in their "last call" stage.

Women in their late 30's or 40's who are divorced (or who have given up on the idea of starting a family) would be more open to the idea of a casual fling with a younger guy.

Those late 30s/early 40s divorced women are often moms already. They would be more open to a casual fling but most of them still won't be dating younger men.

Late 30s/early 40s childless women often are into childless men near the same age.

 

[Hamurabimbi]

She was 33. I was 25. She was a coworker. Things just happened. There was no plan.

Another occurrence a few years later. Me late 20’s. Her early 30’s. We were both students in a post-graduate program. Again. No plan. Just happened organically.

 

[SW15]

something about these mature ladies move me. It's weird but I guess I have to try at least once to know what it's like.

I would have thought you might have had this phase a few years earlier in life. It is common for some of the youngest men (late teens/early 20s) to fantasize about a 30+ woman.

Elevate your game to get with the youngest women. You won't have their attention forever.

I find young ones (~18-25) attractive too. And of course they are my main goal.

Your head seems to be in the right place on this.

Modern dating? There will HARDLY be any difference. A 50 year old woman basically demands the same as an 18 year old woman.

Gen Ys/Millennials in their early 40s are the original participation trophy children. The participation trophy started coming into fashion as part of self-esteem boosting parenting and schooling that was common in the 1990s-early 2000s.

This made Millennial women extremely entitled once they became adults.

A 50 year old woman today is a Generation X'er. While X'ers were not as coddled with self esteem boosting as Millennial, X'er single women have been demanding. In the original "Sex & the City" TV show (1998-2004), 3 of the 4 characters were supposed to be early Gen X'ers. The 50 year old women of today were later Gen X'ers who were influenced by women like those in their early adulthood.

 

[Travel memoir21]

I don't know if you liked @Travel memoir21 's advice ironically, but dear God please do not listen to any of that.

I do fine dressed in f***ing t-shirts and jeans, I don't bring a damn dog or wingman anywhere, and you best not be packing some God damn business cards thinking they're gonna get you laid.

The goal is not always to get laid…its to find and attract Quality Good woman or women who can
enhance your life. The type who will nurture you, spiritual, God loving, Noble, have integrity and will do the right thing….sometimes being friends with those types of women is superior to being in a relationship with a ho bag.


Seeking to get laid with just about anybody is a good way to drain your life force and have unnecessary drama….that you don’t need.

 

[characternote]

Man, i'm far from some super handsome stud, but I find myself turning these older women down even if i'm in a dry spell.

I think that confidence and humour seems to carry more weight with the older women in my experience.

I tend to go for the ones half my age lol. Million times more difficult imo. This sort ideally (personal taste. I learn from the 'post your 10' thread that we all have WILDLY different ideas of what a hot girl is! I genuinely wouldn't even want to sleep with some of the '10's' in that thread, and i'm sure that there's guys here who would turn this girl down)

 

[RangerMIke]

How to do this? Just try... if she prefers younger dudes you have a shot.

 

[Divorced w 3]

Bars and tinder for casual hookups.

I think this type of situation requires a certain set of mentality on both sides.

The only time I shot at a 10+ age gap was when I was 22, and I had met her as a waitress at a restaurant my friends band was playing at. She was an airline stewardess (apparently by the way, using this term now is massively unpopular with women lol) - who was working her side job. She had a ‘crash pad’ near the restaurant and airport, we hooked up there a couple times.

I saw a different example a few weeks ago : the female therapist filling in for my regular one on my psychedelic integration was a super hot, like 9.x and we clicked hard; I had her emotionally invested, she was telling me about her father and was welling up with tears, it was total anchoring on my end, my complete abuse of the patient client relationship and I was ready to drill her and I was thinking about where in the room to do it. It was a great session and I thought about asking her for her number, she was 9 years younger. Would you believe she was married to a guy 9 years younger. I had looked her up bc I didn’t want to mess my situation up with the therapists office just in case. I have no idea where they met, I am guessing something more meaningful than casual sex but you never know.

 

[Divorced w 3]

Sometimes I tend to find women that are slightly older than me attractive. Let’s say I’m 25 years old, and they are 30-35 or sometimes even around 40s. I’ve cold approached some of those but it never got anywhere. They showed some interest throughout the interaction, and I've even got a few numbers but they didn’t respond to my texts afterwards.

This by itself is not enough of evidence that I won't have success with these women anytime soon, but even in the sets oftentimes they will hear my age, and then just have the mental block, on a logical level, that this man-to-woman thing between us is not going to happen. And they usually share their objections in the conversation. Or it just might be an excuse for their lack of attraction to me, but I can't confirm that yet. Most of them seemed somewhat intrigued.

I know that according to social conditioning and hypergamy, it doesn't make sense that an attractive 30-35 years old woman will date a younger guy who is nowhere near her "level" in the main fields of life. In my mind, I think such a woman would be aiming at successful men at their peak SMV, who can provide luxurious experiences for her, raise her status in society, grant her access to opportunities, build a family with her, and treat her like an experienced man would (?)

And so according to my logic, the only thing I can provide them in such case is: good time, adventure, emotions, "fun" + the fact that I boldly approach them in public and try to seduce them without hiding my intentions, which they seldom experience in this way. However, most of them seem to be already over that fun phase, and now are more pragmatic than ever. I guess the only possible path to success in such a scenario is to "game" them hard, have a strong masculine frame, be smooth, and avoid at all cost everything logical. But since they are more mature, this is not that easy.

(I haven't tried it lately, so more evidence might be needed to get a full sense of how it works or why it doesn't. Might post updates here later this year.)

What's your take on this?

I’m going to compassionately tell you that you are thinking way too much. I would agree that certain demographics are going to be easier than others, due to social norms. By definition, lower probability pursuits are probably going to require more attempts. Like anything, it’s possible that you could hit early but that doesn’t seem to be the case here. The only way to be successful is to keep trying.

 

[GoodMan32]

I think I'm starting to understand your stylistic inspiration:

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When I made a move on that 35 year old woman at 23, my style was a lot different.

At 23, I dressed like a suburban teen at a public high school (I mainly wore hoodies, graphic t-shirts, etc)

 

[Gamisch]

I think I'm starting to understand your stylistic inspiration:

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Tons of differences between them.

Dude in the second picture obviously is a gym rat, his posture is way more masculine then the first one. It's not even in the same league.

 

[Fortune_favors_the_bold]

Hit me up, we can try to arrange that magic formula they used in that comedy movie from the 90s and hopefully we can swap bodies.

That way you can have all the spinsters and the HR style professional corporate Biatches while I get the fresh ones in their 20s.

I keep my properties and you keep yours ofc.

 

[nismo-4]

The old woman cope AGAIN. It's just an escape route, nothing more nothing less. A weak excuse.

Modern dating? There will HARDLY be any difference. A 50 year old woman basically demands the same as an 18 year old woman. Ofcourse we can argue there will be nuances, but in general ALL women now want the same: a somewhat good-looking man who can take care of himself, carries himself with confidence and can "handle " a woman.

You won't get an easier way out, sorry OP.

Everything in dating has nuance and outliers. I'm trusting my investment strategies to make millions and long-term wealth.

The wall is a cope too. A woman on "My 600 Pound Life" has more options than most men. The wall is nonexistent, if not heavily padded.

Guys, older women play games and demand the same S-tier guys as someone 21. Women nowadays have at least 5 inboxes. I dated a realtor who was 62, had Atlanta Falcons players in her inbox, as well as high date offers i.e. Nobu, trips to Hawaii, Super Bowl, etc. She showed me this after I destroyed her vagina. Then she wound up with the guy that took her to Hawaii, he proposed to her there. She had the nerve to send me a video of her making out with the guy, he's 62 BMW. AFAIK they're still married. I no longer talk to her. I'm not having anything else to do with her either.

Social media influenced all this. Simp culture doesn't help. A new 2024 Mercedes S-class costs north of 100k. A 2004 Mercedes S-class costs north of 100k. Simps are willing to buy it!

If only they invented marriage, relationship, and dating insurance.

 

[SW15]

The wall is nonexistent, if not heavily padded.

Roosh said this about The Wall in 2014 and it's even more true in 2025.

The Wall Is Softer Than We Think

older women play games and demand the same S-tier guys as someone 21. Women nowadays have at least 5 inboxes. I dated a realtor who was 62, had Atlanta Falcons players in her inbox, as well as high date offers i.e. Nobu, trips to Hawaii, Super Bowl, etc. She showed me this after I destroyed her vagina. Then she wound up with the guy that took her to Hawaii, he proposed to her there. She had the nerve to send me a video of her making out with the guy, he's 62 BMW. AFAIK they're still married. I no longer talk to her. I'm not having anything else to do with her either.

Social media influenced all this. Simp culture doesn't help. A new 2024 Mercedes S-class costs north of 100k. A 2004 Mercedes S-class costs north of 100k. Simps are willing to buy it!

Women in their 50s and 60s today have no shortage of men. Most will end up using online dating where men will simp over them. There are a lot of beta male simps in their 50s and 60s now.

It is wild that a 62 year old real estate agent had professional athletes between ages 21-35 wanting to slam her pussie and offers for expensive trips and other luxuries to get her pussie. There are even simps who would have committed to her and one proposed marriage.