How To Pick Up Older Women

Are you looking for ways to pick up older women?

Then you are not alone. There is a reason why MILF category is one of the most searched categories in a lot of adult sites.

Older women tend to carry themselves with ease, and they usually know what they want, and this energy can be infectious.

On top of that, an older woman who takes care of her body stands out among others, and that can be incredibly attractive and sexy.

I have had my fair share of experiences with older women in my 20s, and I want to share my experiences and bust some of the myths surrounding picking up older women, so let’s dive right in!

Be playful

Many men wrongly assume that they need to be more formal and proper when they interact with older women, and this could not be further from the truth.

If anything, older women desire a man who is able to be carefree and playful around her.

I am not saying you need to act like an immature little boy who does not have any sense of personal responsibility.

But, you need to realize everyone craves for that feeling of lightness. We all enjoy being around someone who is able to make light of a situation that most people would stress over.

Your ability to remain playful under a stressful situation communicates a higher degree of emotional maturity.

It tells an older woman you are emotionally resilient, and you are someone she can rely on.

I once talked to a woman standing outside the bar, and she was in her mid 40’s.

She was standing by herself, and I initiated a conversation by teasing her about how she is all alone without any friends.

During our conversation, she occasionally smiled at what I said, and I would tease her about how she looks like a little schoolgirl when she smiles, while I was stroking her hair as if she is a little girl.

Sounds ridiculous eh? But, she absolutely loved it (In case you are curious, I did end up meeting up with her for the second time and things happened, but a gentleman never remembers…).

A lot of men have these mental barriers that they create in their head regarding what they can or can’t say to an older woman.

You need to destroy those pre-existing biases you have about older women and treat them like how you would treat younger women.

Because think about it, isn’t that what older women desire after all?

No older woman wants to be treated like an older woman. She wants to feel youthful again.

And you are giving her exactly what she wants by bringing out your playful side when you interact with her.

Lead her

Just because she is old does not mean she wants to babysit you on your date.

Every woman wants to be led by a strong leader regardless of her age.

I’m not saying you should be a dictator in a relationship. You should, by all means, welcome her input when making decisions.

But, do not hesitate to make suggestions on what to do when it is time to make a decision.

A bad decision that is swiftly made is a lot better than a good decision that took ages.

For example, when you are trying to decide which restaurant to go, and she doesn’t have any particular preference, then go ahead and suggest eating at your favorite restaurant.

A lot of men spend a significant amount of time trying to figure out what a woman wants, and they try to cater to a woman’s needs every step of the interaction.

But, they don’t realize that is not really what a woman (old or young) wants.

She does not want to be in a romantic relationship with a doormat who always puts her needs first before his.

She wants a man who knows what he wants and is not afraid to express his desire.

A woman, regardless of her age, will feel a lot more attraction toward a man who is decisive over a man who always tries to make the most optimal decision by taking his time.

When you demonstrate your strong leadership to an older woman, she will not care if you are much younger than her.

In fact, your age won’t even cross her mind if you become a strong leader who is able to take charge in a relationship (whether it is casual or serious).

Be sexual

As we have already mentioned, older women usually know what they want.

So, it is often better to be more straightforward with your desire rather than being too subtle about it.

In fact, a lot of older women are flattered when you are extremely sexual with them because it is rarer for them to experience such emotion as they get older.

Men face a lot of shame associated with expressing their sexuality in this day and age, thanks to the rise in feminism and a societal pressure that encourages castration (figuratively) of men.

They would rather talk about weather and little puppies than being honest with their sexual desire.

It is not an easy task for most men to let a woman know that she turns them on sexually.

But, this is something that you absolutely need to cultivate if you want to quickly establish sexual rapport with women you meet for the first time.

So, don’t be afraid to let older women know that they turn you on, and you would do terrible things to do them (with their consent of course…).

You would be surprised to see just how receptive they can be to your forwardness.

Compliment her

Women, of all ages, enjoy receiving compliments about their physical beauty.

But, young and beautiful women are constantly bombarded with compliments whether it is at school, a bar, or the club.

When you compliment them, it will often backfire because they are so used to it, and you will automatically be categorized as another “nice guy” in her mind.

Don’t get me wrong. Younger women love receiving compliments as much as older women. It is just that those compliments are usually not going to translate into her getting curious about you.

Older women, on the other hand, receive a lot less validation compared to their younger glorious days.

It is rarer for them to receive compliments on their physical beauty on a day-to-day basis.

So, it naturally arouses a stronger emotional response when you give them a genuine compliment.

I usually advocate men to stay away from complimenting a woman, but this is one of those exceptions.

You should, however, still stay away from making cheesy or disingenuous compliments. Those compliments don’t serve any purpose other than just making you look bad.

Let me give you an example of how you can compliment a woman in a way that actually makes her feel something.

I need to warn you, however, that it can come off as EXTREMELY cheesy depending on how you pull it off.

And that is why I tend to shy away from giving specific examples over in written words, since 90% of your communication with women depends on “how” you say your words.

So, keep that in mind with the examples below.

The not-so-great way to compliment older women…

“Hey, I am mesmerized by your beauty. Can I take you out please?”

A better way to compliment older women…

Stare at her face or certain spots in her face for a few seconds without saying a word, and she will likely feel a little insecure and ask what you are looking at.

You then ask her if you can be honest with her about something, and that will, of course, make her curious about what you are about to say.

When she urges you to say it, you tell her, “Even your wrinkles can’t hide your beauty” with a cheeky smile and a wink.

If you just looked at the bolded quote, it will probably come off as extremely cheesy.

But, what allows it to not be cheesy is how you say those words, and the way you led into saying that line. And when you dial in those two, it would have aroused a much stronger and a wider range of emotion in her.

Do not be needy

This is a universal rule, but it is especially important with older women.

Older women usually have more responsibilities with the work they are doing, or they may even have kids to take care of.

You do not want to show any behaviors that can potentially make them think you will be more headache than what you are worth.

You do not want her to think that you are just another kid she has to take care of.

So, how do you be non-needy in the context of “picking up” older women?

Here is one example.

Let’s say you are talking to an older woman, and you ask her what day she is free to hang out this week. She says she is busy this week, but she may have some free time next week.

What do most guys do in such a case?

A lot of men instantly jump into asking her what day she is free next week, so they can “confirm” the date.

What you want to do instead is to just be chill about it, and tell her you will text her next week, and you guys will figure something out.

Remember that the more eager you are, the less room you give women to participate.

If you always jump at each and every opportunity to see her, how can you possibly expect her to take you seriously?

Tell a story to set the frame

Telling a story is a great way to make older women feel more comfortable hanging out with you.

Storytelling is infinitely more powerful than direct statements because it allows information to penetrate into someone’s brain with the least amount of resistance.

Take this for example.

Which statement do you think will be more effective at communicating your value between the two?

“Girls love me”


“I had a handful of relationships that turned sour after we broke up. One of the most memorable ones is the girl who turned completely crazy after we broke up. She blew up my phone 24/7, and started even stalking me. You would think she would have better things to do since she was modeling for one of the biggest agencies in the country.

Do you see how you are “subtly” communicating your value when you tell a story (by implying you are so high-value and attractive that even a top model wants to stalk you) as opposed to stating your value directly which will make you appear try-hard 100% of the time.

So, what kind of stories should you tell?

If you have any stories about dating an older woman, it is great because it will communicate that you don’t just want her because of some weird fetish or mommy issue you have.

Another good story to tell an older woman is a story that expresses your belief on how age is just a number.

One of my favorite stories to tell is about how I became friends with guys who are about a decade younger than me when I was traveling to other countries.

And I’ll also talk about how it is not so much the age that matters but the type of energy that the other person puts out, when it comes to deciding who I want to spend my time with.

When you are able to tell stories in a convincing way, you can very well make her think it is the greatest idea ever to be picked up by a younger man.

About the Author Jon Go

I was Introduced to the world of seduction after being a virgin for the first 26 years of life and being dumped by my first girlfriend at the age of 28. The dating world wasn't so kind to a 28-year-old Asian man who barely had any experience with girls. But, I eventually cracked the "code" and began "attracting" two to three new girls a week on average when I was actively going out. I'm not mentioning that to impress you but to impress upon you that you can take your dating life to the next level... IF you are equipped with the right knowledge and a desire to take massive action.