How to Text an Older Woman: The Step-by-Step Guide

You’re into a woman who’s your senior. And you want to impress her and show off your maturity.

Excellent. This article will tell you how to text an older woman and get her excited about you.

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Texting and dating an older woman comes with many prejudices. Myths like ‘all older women are boring,  married, or want a relationship” will be countered with evidence in this article, followed by texting and dating tips on how to meet these interesting ladies.

Why you should also date older women

  • Relationships with mature and experienced women are more stable. Research shows us that most relationships between a cougar (a middle-aged woman seeking a romantic relationship with a younger man) aren’t usually just flings.
  • Better sex. Multiple studies show that couples over 50 have the best sex. Largely because they feel okay about their bodies and aren’t afraid to say what they want.
  • More options. A woman with a career can give you a far better dating experience than a student who’s living off noodles and ketchup on toast.

1. Be more direct

This is why many older women seem bored over text and lose interest. You’re wasting her time. Mature women aren’t boring at all.

She’s simply already been where the younger girls are still heading.

So she’s seen and played all the games before.

Younger girls love it when you slowly tippy-toe your way into her panties. A mature woman, however, often prefers more directness.

But be careful, this does NOT mean you can skip the teasing and flirting, and go straight for a meetup or hookup.

See my next video for tips.

2. Give her room to breathe

My god, I was shocked when I started to better understand older women. One thing that quickly became clear is that these ladies are often looking for… freedom!

Many dudes assume that of all women, the older ladies are dead set on finding a relationship. I’d say that’s wrong.

Usually, the younger ones are looking for something serious. You know, inexperienced girls who binge on movies like The Notebook and still believe in Hollywood love.

Older women, however, are not as naive. They’ve been through their fair share of relationships and heartbreaks. The result? They’re more focused on themselves and their own growth, whether it’s personal or career-wise.

Oh btw, it’s also proven that older women want more sex. Let me just throw that out there.

And even those women who ARE looking for a relationship can be persuaded for something more short-term. The way you text her influences this, but more on that later.

3. Just say hi

Did you think all older women are off the market?

I’ll let the facts speak for me:

In the United States 35% of women between 30 and 55 are not married.

In the United Kingdom 40% of the people between 30-34 are single.

By the time they get to 50-54, numbers go down to 10%.

Don’t assume they’re married, just take a chance and see what happens.

4. Act your age

Chatting with an older woman as a young guy is counter-intuitive. You can just feel that she’s so different from all the women your age. So you make the classic mistake that turns her off.

You try to impress her.

Because you feel she’s so far ahead of you, you want to show that you also have plenty of life experience. You’re not just a silly kiddo. You’re as much of a man as the men of her age.

Little did you know… that’s the opposite of what she wants from you. Know what a younger guy pretending to be all mature and seasoned looks like? Like a 50-year-old wearing the same clothes as his son, trying desperately to be hip.

5. Text like a grownup

There’s one way of texting that’s more typical for younger guys… and it’s a massive turn off to older women. In fact, it’s a huge turn off to girls of any age.

72% of participants in a Zoosk study said they are less likely to text back if someone makes spelling mistakes in their texts.

Heyyyy 😜 ever been to cocktail bar death & company? They have gr8 drinks their!! 😜

Do you know what texts like that make her think of? The ball pit at McDonald’s. In fact, she’ll gladly buy you a Happy Meal if you stay there while she drives off.

Want to make her feel more attracted to you?

Proofread your spelling and grammar, and keep those childish emojis out, because all your immature text message did was emphasize the age difference. In a bad way.

Holy Tip:

For more mature and attractive texts, check out this.

The 10 Texts That Always Work.

A collection of messages my team and I still use with great success to this day.

Download ’em here for free.

6. Be cool with the age gap

Has this ever happened to you? You meet a beautiful mature woman in a bar or on your college campus and you hit it off. Things are going great. But then she asks your age.

You tell her the truth with a face full of shame and her reaction isn’t what you hoped for.

Even though the whole conversation felt great, suddenly you’re “too young for her.”

What went wrong? She could tell you were unhappy with your age. You effectively turned yourself down before she said anything. And that’s unattractive.

The key is to embrace everything that you are. Age and all. And pretty much behave like you usually do.

Research shows that confidence is one of the biggest turn-ons for older women.

7. Embrace your youth

Here’s how to make older women like you.

Fully embrace being the younger, less experienced, youthful, fun, and energetic person.

The young guy who makes himself seem older, wiser, and more mature than he is, ends up:

  • Telling lies.
  • Making up a persona that will break down sooner than later.
  • Destroying his self-confidence in the long run.

All that acting gets him nothing. Because guess what she really wants.

This study, and this study, shows that she deeply desires to:

  • Feel young again.
  • Feel sexy.
  • Feel desired.
  • Feel powerful.
  • Enjoy her sexuality without judgment.
  • Experience the crazy lust of a young guy.

Stop overlooking all the qualities you already have.

It’s when you started acting like something you’re not (in order to get her to like you) that you screw up and scare her away. Oh, the irony.

8. Send her an irresistible first text

You found a gorgeous older woman and want to start a conversation

…but what opener gets her interested, and makes her text back?

We already learned that behaving in a special way just because she is older won’t get you anywhere.

In fact, my #1 opener works on older women really well.

The image above shows me sending the first text to a Swedish mother that was all sorts of hot. What did I say? It combines self-interest with clickbait.

It’s my opener that has the highest chance of getting a response.

I explain how to use it, and what texts to follow up with in this private video. One of the example conversations in the video is with this older woman.

Check it out and then try it out for yourself!

9. Show your intentions (with screenshots)

I’m about to show you how a young, broke, exam-failing Louis seduced a successful and stunningly beautiful woman who was 11 years older than me.

The first rule you want to obey? Don’t hide your intentions.

BUT… This doesn’t mean you do this:

Hey, I’m glad we matched because I really want to meet an older woman.

(I hope it’s clear why you shouldn’t text this. If it isn’t clear then just keep reading and it will be.)

If it isn’t clear to her that you think she’s sexy… then you’re failing. That’s why I’ll often casually tell my match what I have on my planning.

The subtext of the above message:

  • Something casual.
  • Light tease.
  • Heavy flirt.

In general, teasing with age is an effective strategy when texting older women. But it can also be overdone or done poorly. More on that later.

One pitfall with teasing too early is that it can push her away. That’s why I had to pull her back in. Read all about it in the next tip.

10. Compliment her

This is how to get her hooked on your texts.

Playfully push her away with a tease and then pull her back in with a compliment.

Many women will eventually throw an age related question at you. In my case, she asked me (based on the screenshot from the previous tip):

And an “old” lady really turns you on?

How you answer will decide your success. What do you think the best answer is? Anything that makes her feel good about herself.

Older women like younger men because their attraction makes them feel extra sexy. And since she’s getting a day older, she probably has some insecurities about her fleeting beauty.

Hence why I replied like this:

And an “old” lady really turns you on?

It’s mostly your face that does the turning on

Later, when she sent me some photos, I replied:

Not so bad for a 36 year old

Which is a backhanded compliment and also my favorite kind of compliment. But be careful with the age-related remarks…

11. Tease her in all the right ways

Here’s how to deal with the age gap the right way.

Most guys act overly excited about the age difference and ruin everything. “It’s so hot that you’re 10 years older than me.”  Don’t tell her anything like that.

Save that for when she’s already into you and you’re both naked. Until then, your goal is to seduce her by being extra flirty and playful. How?

Playfully exaggerate the age difference.

In this case, I quickly started calling her grandma. To which she responded by calling me toy boy, kid, and child. This makes flirting and teasing easy for the rest of the conversation.

You’re welcome baby

The double meaning when you call me baby

By showing her that you are comfortable joking about the age difference, you show her that you’re fine with it.

And that’s important. If she notices you are doubting yourself, you’ll be dumped in no time.

12. Use your voice

There’s a way to quickly impress an older woman over text.

Replace your texts with voice messages and calls.

If you’re confident that you can hold a real-time conversation and keep it fun, then go ahead and give her a call sometime.

Holy Tip:

When calling or recording voice messages, make sure you’re doing something else at the same time.

While talking to her, the simple act of washing the dishes or going for a walk, distracts your mind just the right amount to sound just that extra bit careless.

If you’re calling your crush while standing still, focusing on the conversation 100%, it will feel like the most important task ever.

Kick a ball around, throw it at a wall, clean your desk, play with your pet…

It’s just a casual call between two cool people of equal value.

Be sure to warm up your voice first. So that the first time she hears your voice, she thinks you just won the Sexiest Male Voice Award.

13. Remove all the filters

Here’s how to get so much confidence that it starts oozing out your di–, uhh, ears.

Stop filtering yourself.

Even on photos or your text messages. Yes, Instagram filters can make you look twice as hot. Your skin will seem flawless and wrinkles will vanish. (I’m not sure about you, but I’m 34 and boy, my wrinkles are popping up everywhere.)

But when you send a photo directly to one girl, and you put a filter on it… then you’re really saying:

“I want to look my very best for you because I really want you to like me. And I’m not happy with the way I look.”

In short, you’re showing that you care far too much about her opinion of you. And that’s a turn-off when you barely know her.

14. Ask her out with confidence

Here’s by far the best way to ask a girl out over text.

Or if you prefer to read, I’ve written an extensive guide on how to ask girls out over text.

15. Five tips for the perfect date with an older woman

Here are 5 simple rules for your date:

  • Groom yourself. Get a haircut, trim the beard, spritz on a little perfume, and wear clothes that compliment your body type.
  • Keep it flirty. She loves your young vibes, as long as you play with her instead of your Tonka Truck.
  • Figure out what she wants. Not all older women are the same.
  • Be straightforward. She knows all the games and she’s not into that. Just be real, just look at the next screenshot.

And for the final thing that will make your date a huge success…

text in between dates.

Even if the date is set, going stealth mode like Tom Clancy will probably get her to flake on you.

Looking for inspiration?

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