How to Text an Older Woman | 10 tips to make her want you

Written by Ryan Cross

Maybe you wonder how to text an older woman you know from work or your social circle. Or maybe you matched with her on an online dating app and unsure what to text to her.

Texting to an older woman is slightly different in many aspects than talking to a girl who is just finished high school. Above the age of 30 to 35, women have entirely different ambitions, life goals, and preferences about guys than their younger counterparts. That’s why you need to text them with a different mindset.

How should you text an older woman?

As women get older, masculine personality traits become progressively important while physical appearance less critical to them. When you text an older woman, use confident language, tease her, tell her compliments about her personality and make her laugh.


This blog post will help you make older women (or one particular woman) become attracted to you and go on a date with you by providing texting strategies tailored precisely for them.  

Why text differently to older women?

Attractive young girls are very picky when it comes to dating guys: they often want the very best or no one. Other times they look for extremities, like very tall, wealthy, or popular men. Younger, hot girls tend to date a lot of men, and many of them end up having a lot of one-night stands without worrying about consequences.

As they get older, many circumstances change over time, which affects their dating strategies. Even beautiful women notice a decrease in their sexual market value which eventually forces them to change their dating strategy. Personality becomes crucial, while appearance not as important as it used to be.

Older women still have a high sex drive, so many of them seek guys for one-night stands. Although many now want security instead of excitement and future provisioning instead of exciting adventures with a man.

Older women don’t feel sexy enough even if they are hot.

In their late 20’s, early 30’s, almost every woman experience a serious paradigm shift in their way of thinking about men. 

In their early 20’s, even average-looking girls can have a tremendous amount of dating options with guys. But as they get older, after around 27-30, they experience a drop in the amount and quality (attractiveness) of potential dating partners.

Namely, they aren’t as popular as before. Of course, there are plenty of hot women in their 30’s who can still date many guys. Nonetheless, they feel that year after year, they get less and less attention from men.


The decline in women’s relative attractiveness in their late 20’s has three major causes:

  • The most obvious one is that they are getting older, and by nature, they slowly lose their attractiveness
  • New competition arrives who have several years of advantage in terms of attractiveness.
  • The number of potential dating partners decreases because men are getting married or choosing hotter and younger girlfriends.

What do older women want in men?

Besides physical attractiveness, women seek evidence of power in guys. Through thousands of generations, women’s minds have developed in a way to not only seek physically attractive men but men who also possess power. 

Power has a thousand forms (wealth, confidence, control, expertise, ambitions, etc.), but EVERY woman finds some of them sexually appealing. Also, many forms of behavior turn every woman off because it indicates that the guy lacks power.

You may ask, okay, but how does this apply to texting an older woman? 


Older women want powerful men

Women often change their dating tactics after they’re over 30. They focus more on high status and masculine personality, while appearance becomes less important to them. Of course, the better you look, the easier it to date a hot older woman. Yet you can get her interested if you show your confident, dominant, decisive, and laid-back side.


Here are my best tips to make older women attracted to you over text:

Don’t try to impress older women

Common mistake guys often commit is that they try to create a fake older and more mature persona to live up to older women’s expectations. But the reality is that if an older woman matches you on Tinder, she did it on purpose. She doesn’t want a 35-year-old personality in a 25-year-old guy’s body. She would like to talk to you because you may have several great qualities that men of her age lack.

Behave as someone your age should behave

The odds are on your side if you want to date an older woman because you have several advantages compared to older men. You probably have more energy, a healthier body, fewer wrinkles. Women love to date younger guys because they also feel younger with them.

You don’t really need to buy new clothes and grow a beard to impress older women. It’s enough to act and behave like it is expected of a guy your age.

Of course, a certain level of maturity is necessary to attract older women. An average 20-year-old boy will have a hard time seducing a 36-year-old businesswoman. But don’t use maturity as a dating tactic to impress them. Use it for your self-development. If you start focusing on masculine qualities that women generally consider appealing, you can raise your status and attractiveness:

  • Include photos where you dress more casual
  • Show your awesome life
  • Use confident language (more on that later)
  • Improve your flirting skills
  • Know how to turn on women

How to text an older woman for the first time?

Texting an older woman for the first time is very similar to text a 20-some girl. But there are a few exceptions to keep in mind when you’re about to send your first message to an older woman:

  • Avoid slangs and abbreviations
  • Don’t overuse emojis
  • Don’t mention her age even in positive ways because it only causes trouble
  • Don’t mention your age, because it’s completely unnecessary and it also causes trouble

I have a magical yet unknown online dating opener that got me literally hundreds of dates over the years. It goes like this:

Of course, it has many variations, but I always keep the structure:

  • 3 “high-status” and
  • 3 lighthearted and funny facts about me.

Feel free to come up with your own version, but never use needy compliments such as “You looked so beautiful that I fell in love immediately.” Also, don’t try to be very funny, because it can backfire if she doesn’t understand your humor.

For older women, confidence is more important than looks


The most profound way to show your confidence to an older woman over text is to use confident and affirmative messages. 

Making statements from questions puts you in a power position and places her in a situation where she is the one seeking authority. 

For example, instead of saying something like “Do you want to hang out?” you can say “Let’s hang out” or “We should hang out.” 

But it works with other general questions too. Instead of asking her, “Do you like dogs?” you seem a lot more confident by forming it into a statement: 

Another awesome way to show your confidence is to assume that she is already into you and act accordingly. 

 “Treat her like she’s the one who wants to be with you, and therefore, she has to work for you.”


This behavior will change the dynamic and position you as the more powerful one, which is the foundation of sexual desire. If the woman teases you back, it’s a great sign. 

But be aware of keeping this kind of texting funny and lighthearted because it only works in this way.

Have the same fun with her as with younger girls

As you can see, older women are basically the same as younger ones, with some minor differences. They also like to have fun, dive deep into meaningful conversations, or be aroused by an attractive guy. Women – be old or young – crave to feel the excitement, passion, desire, and fun. If you can elicit strong positive emotions in older women, you are on a great track to date her in the foreseeable future. Here are the methods to do so.

How to tease older women?

With teasing, you can create a delightful atmosphere and establish a subtle dominance with her, which is the prerequisite to turning her on later.

You want to establish the playful back-and-forth teasing because this is the foundation of establishing a sexual vibe with her later.

To be honest, I don’t really tease older women with their age. It can certainly work, but I find that it has more drawbacks than benefits. Besides age, I never tease anyone with her religious and political views, with her body and family/friends because it can easily be interpreted as an insult.

How to make older women laugh?

Humor works exceptionally well with older women because it not only conveys great feelings to her but also shows that you aren’t intimidated by her age. The best way to make her laugh is to be funny and confident at the same time:

How to flirt with older women?

Why send flirty messages is a great way to build a deep and intimate connection with an older woman? It’s because women desire to be desired by men. 

Women find guys more appealing who flirt with them, and they are turned on by men who make sexual moves on them.

Women are flirting addicts for the simple reason that it’s fun, and they can connect with guys on a more emotional level by flirting with them. Flirting adds a fun sexual component to the conversations and sparks excitement out of women you talk to.

Be cautious with compliments

I have no doubts that every woman likes compliments. But there are mistakes that many guys commit. Here are the basic rules for complimenting older women:


Compliments should only be given unconditionally


Somewhat attractive women are fed up with compliments such as “you have a gorgeous face” or “hot body.” Not because they don’t like compliments. But because they see through the goal of these texts.

These kinds of compliments have two negative sides:

  • A lot of men make such compliments to get something back in return—most frequently sex, reinforcement, and affection.
  • Women think that they have to reciprocate these compliments. And the obligation is the main killer of attraction.

Don’t mention her age

I’m sure you have good intentions when you text her this:

“You look a lot younger than women at your age.”

But this compliment has an underlying message:

“Women in this age usually don’t look as good as younger girls.” Maybe it’s true, and maybe many older women are happy to hear such compliments, but it can also create friction in her.


Non-physical compliments are the best

Older women – especially hot ones – are fed up with physical compliments because those are mostly given by desperate guys. I never talk about how hot I think she is. Instead, I focus on her personality.

If you really want to make a compliment on her looks, try a non-needy, non-pushy, and definitely non-sexual way:

What to ask from an older woman over text?

You can ask a bunch of interesting questions from older women, like:


What do you see differently now than in your teenage years or twenties?

What quality isn’t as important now on guys that a few years ago?

Do you like the same type of guys as before?

Do you think a man should rather be a good kisser or a good dancer?

Should a man be wealthy or good in bed?

What would you choose if you can only choose one in a guy?: Humor or confidence?

What’s the most important object in your life? (Besides the huge dildo in your drawer).

Have you got a weird superstition?

Have you ever done anything you could be arrested for?

Tell me something: if you could have a superpower, what would it be?

What is the craziest thing you’ve ever done?

Would you be infinitely rich, or would you live forever?

What’s something that you’ve never been able to do well?

What’s something from your childhood that used to be common but now is pretty rare?

The questions you ask from older women (and anyone else too) should serve one or two goals: to bring out positive emotions and get to know her a little bit better. With these two factors, you can develop a deeper connection with her.

How to ask out an older woman over text?

In general, older women don’t like to chat with guys for long, so ask her out as soon as you see signs of her interest in you. If she laughs a lot at your jokes, texts a lot, asks many questions about you, you should invite her to a hangout. Be confident and decisive when you talk about your dating plans.


If she had several great convos with you, then she will think about hanging out with you. If she likes you, she expects you to ask her out.

When she enjoys every minute with you, you can successfully ask her out by texting, “wanna hang out?”. 

But if you couldn’t convince her to think of you as a potential dating partner throughout the conversation, then there are no silver bullet techniques to get her to go out with you.

Tease her about meeting with you

When we have a great time during the conversation, I often test the waters by challenging her a bit with dating me:

“I bet you wouldn’t be this confident/cheeky/cocky in person.” 

If she responds with something positive like “I’m WAY funnier in person :P” you are already a step ahead to finally meet her. If she texts something affirmative, you only need to know the day and time to schedule the date.


Plan the date soon

Keep in mind that women’s – especially older ones – attraction is constantly decreasing. The further in the future you fix the date, the more difficult it will be to maintain her interest until then. If she says she is free one week later, I continue texting her without talking about a date.


Find out her programs for the week to know the right time to ask her to hang out with you. If she says she is free on Sunday, you can come up with detailed plans on Friday.


Wait for an emotional peak and ask her out

Women are more likely to accept your date invitation if they are experiencing positive emotions. That’s why you should ask her out when she is either laughing at something or feeling excited or happy.


Related Questions


How do you impress an older woman?

Older women love successful men; therefore, you can impress her by texting about your ambitions, goals, and engaging stories with a confident delivery. You won’t come off as overconfident if you are funny and laidback simultaneously.


How do you know if an older woman likes you?

An older woman likes you when she texts or talks to you frequently, even if you don’t initiate the conversation. You can also tell she is interested in you if she likes your social media photos, wants to meet you, or is interested in your weekly schedule, hobbies, and personality.