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How To Pick Up Older Women: 9 Tips

guy attracting a cougar

As a young guy, women around your age can be a bit hard to chat up at times.

But can you imagine just how intimidating it is to approach older women?

For one thing, due to their experience, they won’t be easy to impress. On top of that, they’re unlikely to fall for the usual pick up methods since they’ve probably seen it all.

In short, if you’re interested in picking up women in their 30s-50s, you shouldn’t use the same tricks that you use on younger girls.

Not only will they not work, but the odds are high that the woman you’re into won’t even give you a chance.

In other words, you need to understand what appeals to older women if you want to get lucky with them.

Simply follow our 9 tips to pick up older women, and you’ll have no problem getting into their pants.


1. Ditch The Cheesy Pick Up Lines

This is a must if you want to chat up an older woman and impress her.

You see, with the right pick up line you might be able to get the attention of a young girl.

Yet, when it comes to older women, cheesy lines won’t have a heavy impact. Actually, they might ruin your chances because she sees you as an immature guy.

Therefore dropping one on her won’t make her think you’re charming in any way.

With that said, simply saying “hello” or starting small talks will give you a better outcome.


2. Wait For An Opening

There’s one thing you need to avoid with older women, and it’s interrupting them while they are busy doing something. They’re fed up with that at this point and won’t stand for it.

So instead of walking up to her immediately, it would be best for you to wait for an opening. Let her finish whatever she’s doing, whether it’s drinking or talking to a friend.

Once she’s done with it, only then you’re in the clear to make a move. But do only if there are signs that she’s attracted to you first.


3. Be Direct And Classy

Since they’ve gone through many things in life, older women no longer have the patience they did in their 20s.

In other words, a middle age woman won’t want to deal with ambiguous guys. Meaning you must have a direct attitude to be successful at picking them up.

Be open with what you want, be it casual or not.

Although, you can’t be tasteless and simply say, “I want to have sex with you.” You still need to be polite about it and show genuine interest.


4. Don’t Play Games

Is this your first time to go after a cougar or milf? If it is, you might think that you can play games with her to get laid.

However, doing that will turn them away from you.

For this reason, you have to convey your true intentions when you’re hitting on a mature woman in real life and online.

Pursuing an older woman is all about being transparent and direct since they don’t like any drama.

They are aware that men are interested in sex above everything else. So don’t pretend otherwise.


5. Focus On Her

Being young, it’s only natural that you’ll have less experience compared to a woman who’s in her 40s or 50s.

As a result, what you have to say may not interest her much. Moreover, it could even expose your weak points and turn her off.

This is why the focus of your interaction should be on her most of the time. Show that you’re sincerely interested in her as a person and as a woman.

Allow her to take the lead in the conversation and explain things to you. She’ll appreciate your honesty and eagerness.


6. Don’t Mansplain

It’s typical for men to always want to control the conversation by bragging about how good they are at something. This article by Business Insider reinforces this since it reveals that over 60% of men like to mansplain.

While you may get away with acting like this towards girls your age, it won’t sit well with older women. Cause aside from being knowledgeable, many of them are accomplished professionals too.

In light of this, you shouldn’t try to mansplain to them. They know what they’re talking about and won’t put up with you talking over them.


7. Be Mature

As they age, women become more confident and secure with themselves. Due to this, a 30+ year old woman knows her value and won’t settle for anything she doesn’t deserve.

As such, she won’t be wasting a moment on a childish guy with bad manners. You basically have to prove that you’re a man to her and not a child.

You can do this by approaching her confidently and being gentlemanly towards her.


8. Get In Shape And Dress Well

Do you want to know the ultimate advantage that young guys have that older men don’t? It’s their looks and body.

Sure, several mature men tend to be distinguished and wealthy, but they also commonly sport ‘dad bods’. As a result, these type of men loses out to the fit and toned bodies that younger guys have.

On account of this, you should get in shape and dress well to pursue a cougar. Even just being lean is enough as they’ll be happy to sleep with you than with a fat old man.


9. Find Out Where Older Women Hang Out

If you expect to meet older women in the regular party spots in your area, then you’re deeply mistaken. All you’ll get at these places are girls in their teens to early 30s.

We’ve already written in detail where to find older women. But in short online, cougar bars and fitness classes are your best bet.

Middle age women don’t enjoy deafening party music anymore. They prefer quiet and classy places to hang out with girlfriends or to use anonymous hookup sites to find sex.


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  • Tom Phillips

    Tom Phillips is a Dating Coach for World Hookup Guides who has been helping men to succeed with women for almost 7 years. His coaching career began with one-on-one coaching and has gradually evolved into seminars. He has dated successfully dated several women over the years and now shares strategies and techniques on several national publications in addition to World Hookup Guides.