Dating Older Women
July 4, 2005 by Thundercat
Filed under Rants & Reviews
Got this email from a reader that sparked my interest…
TC,
Hey man, I read the
blog daily – it keeps my day exciting, no doubt about it.I’m a younger guy,
just turned 23 yesterday, and am totally into dating women in their 30′s. I was
wondering if you could create an article link for PUA’s to discuss this aspect
that is rarely mentioned but many PUAs are still game for experienced women. I’d
love to share some of my insights and hear what everyone else has to
say.Let me know,
TC.DK
Okay, DK, if you want it, here it is. Personally, I don’t think it’s bad to date older women. In fact, if your a younger guy, you can learn a LOT from dating women who are older than you (and many of them are much easier to pick up than the 18 to 25 year olds). So here’s a thread for you guys to discuss everything you know about dating older women.
fpparisshop.com on 
sandyterrace.com on 
Wbgvzy on 
RandallDib on 
DavidLop on 
I like em in their late 20s on up myself. I have way to much exposure to the younger ones 18+ so its getting a little old, not that Im not attracted to them. I have several buddies who are in their early 20′s who have a good amount of chicks hanging with them. Being in my early 30s my interests have difinatly changed. I personaly like the ladies who are entering their sexual peak which doesnt happen until their much older.
A pick up guru who specializes in MILFs now there’s an ebook I’ll throw some cash at. Shit maybe I should write it myself. Hmm.. do I See a niche market comming on.
Older women love to fuck.. and fuck… and fuck some more.. then just for fun one more time.. At least thats in my experience but maybe I just picked the good ones
I was the one who requested this article so, thanks a bunch Thundercat.
Here’s some observations I’ve had about dealing with older women…
Once you’re in, YOU’RE IN and they’ll start to do a lot of the work – throwing around IOI’s, compliments and kino Left and Right. Especially if you’re a younger guy, they know you have tons of hot, younger women to chose from but you chose her. From what I’ve seen, this is very validating for her.
Now, I shouldn’t have to say it but I will. Most guys she meets – esp. the one’s her age – brag about a lot their material trappings b/c they’ve had plenty of time to acquire money, cars, beach houses and super sweet middle management positions
Don’t even bother talking about this, seriously. She deals with dumbass guys flashing their Lexus keys at her all day – and have been for the past 10 years – so go in their and mix shit up in a very artful, charming way. She will reward you enormously for this!
Some of the ways I accomplish this is thru storytelling and game-playing (the good kind). Storytelling is an enormously powerful skill to have with older women. When telling stories, I often weave in references to art, dance, spirituality, fashion and, yes, “Sex and The City” (you would be surprised at the reaction you’ll get by dropping a reference from this TV show). For example, I’ve taken yoga/breathwork classes and studied chakras so, I may make references to how her creativity and joie de vivre strikes me as being a woman who has a dominant sarcal chakra.
To some this might sound hokey but it works. If it doesn’t feel congruent initially, no worries. Read up a little bit on – say – yoga, modern art, fashion, chakras, palm reading and learn a few basic dance steps and think about how you can weave these into your interactions with older women.
These more feminine things, like art, music, meditation are admittedly a little wierd for guys to learn. So, you don’t have to make them your entire routine – keep the conversation light and fun, more than anything – but do a few of these things while in set and you’ll soon find yourself with a cute mom on your arm.
Regarding cocky/funny with older women…don’t bust her balls much b/c they know the score and, I have found quickly, will call you on it. But do have a charmingly difficult and playful attitude, basically just tone down the C/F and replace the “cocky” with “witty”.
Other random notes…
+ Older women are typically very generous and will buy you drinks – I always tell them I’m drinking Grey Goose
+ In my experience, they typically respond to a “Freeze-out” but if you outright start flirting with other girls to make her more jealous, good luck. Like I said, they know the score and will assume you’re just a typical cock-brained 20-something who doesn’t appreciate them.
+ Like all women, they strive to be understood and felt. Showing them that you can do this even a little bit will reap you enormous benefits. Most older women have only felt this way thru reading feel-good chick books, temporarily in yoga class or, even more fleetingly, by watching a chick flick or TV show…let alone by a younger man. You can accomplish this by employing some of the more new-age methods above – chakras, yoga, palmistry. And be genuine with her, guys – lying to women is not cool.
Now that I’ve shared that, how have you guys dealt with the age difference issue that we encounter on nearly every encounter with an older woman? How do you guys move from being “her boy toy b/c she’s desperate” to “her dirty little secret”?
DK
bump
LOL! There is no challenge or game required for younger men going for older women. It’s like shooting fish in a barrel. Just show you’re interested, assume the deal and you’ll be banging her in no time. I’m 31 – I think I know what I’m talking about.
They know the deal. They’re old and you’re young. They know you want them. Don’t play any games. Just meet, bang and go home.
Easy.
Ever heard the joke:
Q: “What do older women and dog shit have in common?”
A: “The older they get the easier they are to pick up.”
Absolutely grand hearing some very simple Cougar Hunting advice….nice, and pretty much right on the money from my experience. I have run into a few situations though..
*I’m 23 but pass for 26 when I dress nicely, I have often run into the age issue with 30+ women.
Her: “So doll, how old are you?”
Me: “How old do I look?”
Her: “I’d say about 25 or 26. How old do I look?”
Me: (totally lying) “Mmmmm, I’d say 28, 29″.
Her: “Awww thanks, how old are you really?”
It never fails, that ALWAYS happens. I’m not about to lie to anyone and end up saying “23″ and within seconds they excuse themselves.
What say you, my man?
DG
Test – sorry!
I dig older chicks. My exgirlfriend is 35. I’m 23.
To me, all chicks are the same accept…older chicks have money. I’m not a pimp and don’t like any guy who lives off of women. But I find it annoying when chicks I hang with don’t have any money. How annoying. They aren’t playing games either. Younger chicks are broke ass chicks. My ex taught me a lot of shit I didn’t know about like how to save money, how to clean, etc. She was great cause she made everyone around(friends, relatives of friends) comfortable and that made it easier for me to soialize. Older chicks have more experience in these things.
common misconception: dating older women, or cougars as they’re often called is not so bad; and these women are not necessarily desperate or predators, in anyway not more than their male counterparts. I think it’s about time that slightly older women date younger men, just to get back at all those grandpa’s preying on girls as young as their own grandkids or daughters. Aside from that; nowadays women in their thirties look just like women in their twenties; so why not cross those age boundries a bit?
Since I requested this post a few months back, I’ve learned a thing or two…go figure
First, for what I want out of a woman – intelligent, witty, sexy, cultured and emotionally available – I’ve found is more available in older women. This isn’t to say that there’s not women in their early 20′s that don’t have this…it’s more than women like this are easier to find in their 30s and have a certain ‘je ne se quois’ about them that I just can’t get over
Regarding the age issue, that I mentioned above. If she brings it up, don’t be alarmed but if she makes a big deal about it, move on. This is a big insecurity problem SHE has and there’s not much you can do about it. If she’s just testing you out and asks how old you are, I’m always 100% straight-up with her. Like, don’t make it an issue and there’s a good chance she won’t either.
For example, the other night I met a very cute woman out and we hit it off well. A few days later, I’m hanging out at her place, getting ready to go out for cocktails with her. After some discussion, she nervously asks me “Uhhh, How old…..are you?” – she had a very concerned look, as if I was gonna run off the minute she told me how she was. “23″, I say. “Oh my god”, she exclaims “you are such a baby! I’m almost 29.” Again, I could tell she waiting for me to freak out or something but I just looked at her and, with a smile on my face, said “Perfect!”. Since then, age has NEVER came up and our interactions have gone very, very well.
Guys, there really is way less drama with an older woman. No bullshit, no catty attitudes with girls in the bar. Just a sexy, independent chick who’s glad to have a cool, good-looking young man around.
DG
From the time of my first experiences, I always had some things going on with girls two or three years older than me, but once I hit college things went through the roof. I used to kinda think of the whole older-woman/younger-man topic as mostly urban myth, until a whole bunch of crazy stuff started happening in my life, rapid-fire. I found out that older women get together with younger guys way more than anyone seems to want to admit. It makes sense that the whole phenomenon remains sort of a secret because a big part of having one of these encounters happen involves first giving off the indications that you can be very discreet. The older women really look for those signs in younger guys. I sort of give off that impression naturally, so I started finding out how much it meant to older women to see that. By the end of my first semester in college, most of the older women in my life started acting different if and when we were ever alone together. I was taken by surprise at who and how many older women are up for a secret encounter with a young guy. It sort of freaked me out for a while at the beginning. But I just kinda followed their lead, and let things happen. It’s good to do that. Whenever you find yourself in one of these potential situations, I recommend a guy just stay calm, don’t talk too much, and just go with their suggestions. I found that my job was mostly just not to fuck it up. They usually take care of all the planning and stuff. Once things progress to sex, it then becomes time for the guy to step up. At least start taking charge a little, to see if it turns her on. A few of them seem to want almost total control in bed, but most really love it when you shift into man-gear when things get physical.
I didn’t start out purposely seeking out older women to hook up with. That came later, and proved to be a more complicated and challenging task. My first several encounters with older women all occurred with ones that I knew through friends or work. I think there is a huge advantage to just being around a woman periodically, or regularly. She starts to see the opportunity, and almost instinctively starts planning something.