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How To Flirt With Older Women Over Text: 9 Message Examples To Seduce Her

guy texting older woman

Flirting with an older woman over text might seem intimidating especially if it’s your first time. But it shouldn’t be.

Actually is much easier and more straightforward than flirting with younger girls. The reason is older women know what they want and also know what you’re after.

As a result, hardly you’ll have to deal with texts like “what do you mean?” or “I don’t understand it”.

And with older women, you won’t be ghosted as often happen with younger girls.

Yet, before sending a seductive text message, you have to consider a few things. Simply because you can’t take the text back once she’s already read it, can you?

To help you nail the conversation, we’ve put together this guide to flirt with an older woman over text.


How To Text An Older Woman For The First Time

flirting over text with an older woman

You may think that since an older woman is into fun and young guys, you can act the same way that you do with girls your age. That isn’t the case at all.

Mature women see the world differently than younger ladies. Simply because they are a different generation than yours.

So there is the possibility that what you truly want to say will get lost in translation if you approach an experienced woman like a 20-year-old girl.

To avoid this, you must remember the following:

  • Spell out every word properly – Since she won’t get the slang or appreciate the shortcuts, your messages have to be clear and easy to read.
  • Don’t assume anything – It’s natural that you two won’t always interpret things the same way. So you shouldn’t hesitate to clarify any topic.
  • Don’t bring up the age gap – No woman wants to feel old. Therefore, unless needed, don’t talk about your age since it’ll remind her how old she is compared to you.
  • Don’t play hard to get – older women don’t play games as they prefer being straight to the point. You have to be honest too, or else she’ll think you’re a child.

Keep these pointers in mind, and you’ll have no problem with flirting and seducing an older woman through texts.


9 Flirting Message Examples to Text Older Women


1. I Had An Amazing Time Talking To You. I Want To Do It Again

There’s no question that women like it when people compliment their looks. But older women have received that kind of praise more than a hundred times by their 40s.

Moreover, it’ll be nothing new to the mature lady you like, especially if you’re going to say something generic.

This is why if you want to be a bit unique, you should target her personality with messages like this the first time you text her. You can add the topic you talked about after the “to you” part.

The appeal: Aside from expressing your interest, this also tells her that you actually enjoyed listening to her.


2. Hey, I’ve Been Thinking Of You…

This text message is a cliché, but it works well. Plus, you can tailor the content to be either sweet or naughty, depending on your target.

For instance, if the older woman you’re into is on the sweet side, you just have to end the sentence with a wholesome compliment. Something along the lines of “and your pretty face” would be good.

Then again, if you’re aiming at an aggressive cougar, you can finish it sexily with, “and wondering how I can get you naked.”

The appeal: The woman you’re interested in will be glad that you’re directly admitting your attraction to her.


3. I Know We Just Met But I Want To See You Again

Did you feel solid chemistry between the two of you while you were chatting? Or maybe you simply want to shoot your shot immediately?

In any event, this is the flirty message that you should send if you want to score with an older woman right away.

Even if you’re only saying that you want to see her again, this text obviously hints at your sexual desire. You’re basically letting her know that you can’t hold yourself back from wanting to see her.

The appeal: Although this text is aggressive, it won’t come off that way since you’re just stating what you feel.


4. If I’d Known I Was Going To Keep Thinking Of You This Much, I Would’ve Gone Home With You

Do you want to sound like a sweet guy yet be forward at the same time?

If so, then this is a fitting first message for you. It’s the perfect text which conveys the combination of your admiration and lust towards an older woman.

Not to mention, you don’t even have to wait long to get it to her. In fact, you’re free to send it as soon as you want. It’ll further prove to a mature lady that you’ve got it bad for her.

The appeal: You’re essentially stating that you want to her without being vulgar about it.


5. I Still Can’t Believe I Got To Meet You Last Night

For guys who don’t want to rush or are thinking of taking an older woman seriously, this is a great message to start flirting over text. It defines your strong attraction to her in a polite and sure way.

Besides that, you’re also inflating her ego when you voice out your disbelief in this manner. What woman wouldn’t be flattered to know that a guy feels this giddy for meeting her, right?

Furthermore, this sort of text message is still believable even if it’s made out of sweet talks.

The appeal: Mature ladies may deny it, but deep down, they’ll want you to keep going.


6. Do You Know Just How Lucky I Am To Have Met You

According to this article by Paired Life, feeding their egos is one of the reasons why cougars are into younger men.

And that knowing that they can still attract a man in his 20s will boost her confidence as well.

In light of this, sending a text message like this will undoubtedly make an older woman happy.

Apart from that, they will also feel sexy and beautiful since you’re telling her that she’s a rare person in your eyes.

The appeal: Women love to feel that they’re special. Hence receiving this compliment from a young guy like you will definitely win over a mature woman.


7. You Looked Amazing Last Night. I’d Like To Take A Closer Look Next Time…

On the whole, women always want to be admired. This means that praising their looks will always have a positive effect when you flirt with them.

On that note, you can even use their vanity to get closer to an older woman quickly. With this type of text message, you’ll definitely let them know how beautiful you think they are.

In addition, you can turn the flow of the conversation into a naughty invitation. Just put a suggestive line at the end, like, “minus the clothes” or “in bed.”

The appeal: She’ll be more than willing to confirm how hot she is to you.


8. My Thoughts Are Full of R-Rated Scenarios, And You’re To Blame

When you’re a confident guy who’s got his eye on a mature woman, this is the text you need to lead you in a sexy direction.

It’s a straightforward and playful way for you to seduce hard without coming off as forceful.

But to have a high success rate, you must at least send it to an older woman who’s showing signs that she wants you.

After all, some women may find it too assertive if they’re not yet interested in you.

The appeal: This is a nice approach with aggressive women since you’ll be seen as a fun and bold man that suits their taste.


9. You Were Waiting For My Text, Weren’t You?

It’s more or less known that women tend to go for funny guys. So sending a flirty and witty text message such as this is typically a good call when you’re texting an older woman for the first time.

And whatever she replies, you can bet that your courage will make a strong impression on her.

What’s more, she’ll think of you in a better light since this text will probably make her laugh or smile.

This will also show her that you’re a man who can handle himself.

The appeal: It’s a fun way to break the ice and resume the mood back to when you first started talking.


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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.