Diamondog's Blog

Hey Diamondog, is it true what they say about older women? If so, how do I go about
dating an older woman, and what's it like once I do?

Like this!  (But remember, only one of them
can be politely called a "cougar")  tounge

Great questions! The great irony of pickup is that the so-called hottest and youngest girls are pretty plain lays. They more or less just lay there quietly and don't do much. But women who are about ten years older than you? Watch out. You better be at the top of your game. They will wear you out.

With that said, here are my 7 tips on how to date older women:

1. Surprisingly, you must be respectful. I say surprisingly because you've been led to believe that all older women have voracious sexual appetites. Yes, they do. But don't objectify her. She must know that you take her seriously as a person, not as a novelty. Never call her a cougarangry

2. At the same time, you must communicate as a man to a woman. Don't talk to her like she's interviewing you for a job. The conversation can be more blatantly sexual quicker than it would otherwise be with a girl your age. You must balance between points 1 & 2idea

3. Be prepared for tests. The most common one is “Why me? I'm old enough to be your mother!” You would think that she would be self-conscious about her age enough not to bring this up. After all, she would not like if you asked her her age right off the bat. Instead, you can pass this test by remaining unreactive, winking and saying “Almost old enough” or something to that effect. Don't flinch or wince. Just like any other test, it matters less what you say than in how you say it.  omg

4. Expect more maturity. Older women are more interesting to talk to. They will appreciate your worldview, as long as it is compatible while being different enough to be interesting. She will also likely take an interest in your interests, provided you are interested in hers. 

5. Expect a surprising amount of energy. The really young girls may just want to lay around and drink during the day. Since the older women usually don't stay out all night, they are surprisingly energetic during the day. They will appreciate your energy, especially when they compare you to the guys their age who have let their own bodies fall apart.

6. Make her feel attractive as you would any other girl. The difference is that she will appreciate it much more, and not think you are trying to manipulate her. Don't let her break your junk off in showing her appreciationheart

7. And now for something much more serious. Here's the reason she may be hesitant to get sexual with you, or continue beyond a one-night stand, even if you're much better looking than the last few guys she's dated. She thinks you may be experiencing puppy love and be unable to let go should the relationship end. That you'll need a lot of therapy and expect her to pay for it. Not what she had in mind when she hooked up with you. So make sure to demonstrate an abundance mentality like you would all the time. That means don't overdo it on points 2 & 6omg so you don't get broken heart

Not this!

So there you have it. Seven tips on how to date older women, for the hottest lays. Post any feedback you may have here, and how you used these ideas when closing in Field Reports.
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Trusted Member

Join Date: 05/14/2012 | Posts: 4166

 Nice man, I wrote an article on dating older women and started with the exact same pic! Lol.

Anyway, you basically mentioned it, but older women (30+) are able to pump up their own emotions so that makes things easier for the guy. That can also make it more chill to hang out with older ladies, cause they're not all crazy if they don't get the emotions they want from a guy. 

Still, older women imo often don't understand that confidence and emotions can be obtained from within. They still often think that the "right jacket" or "best shoes" will make them "extremely confident." 

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