How to Text an Older Woman You Like and Keep Her Interested

knowing how to text and older woman like this is criticalAre you interested in learning more about how to text an older woman you like, and how to keep her interested?

It’s unlikely that you’ll discover any surprises, since dating is straightforward by nature.

Given the rise of text messaging and smartphones, there’s plenty of information out there on how to text women.

But much of the advice just isn’t useful.

We are going to give you useful and accurate advice regarding how to text older women, which is obviously a very particular subject.

How to Text an Older Woman You Like

We’re going to separate the wheat from the chaff and give you pointers that will help you increase your success.

Firstly, allow us to point out the mistakes you should avoid.

These are mistakes you must avoid whether you first met on the street or if you met using an online dating site like those in our annual ranking and review of all the best sites for dating older women.

Mistakes to Avoid

When learning how to text an older woman you like, it’s crucial to start on the right foot.

How are you to get her interested if you’re making a bunch of mistakes?

This is why you should avoid them to begin with.

Generally speaking, the more a woman likes you, the more room you have for error.

So if you’re chatting online or you just recently met her, you have to be more careful to avoid a mistake that could ruin your chances.

One immediate mistake we must mention is texting too much.

Older woman with wineTexting a woman too much when her interest in you isn’t concrete yet is a recipe for disaster.

She might feel that you’re too interested in her, which is essentially overplaying your hand.

Ideally, you’ll keep her guessing, through short replies rather than lengthy responses.

And allow her to ask you questions as well – it’s a reliable indicator that she’s interested in you.

Asking a woman several questions over text and having her reply out of courtesy is not the way to keep her interested in you, provided she is to begin with.

Which leads us to the most common texting mistake, which is showing her that you like her too quickly.

If she hasn’t yet shown you that she likes you – by asking you questions, giving you some sort of compliment, or inciting conversation – there’s no reason to be forward with her just yet.

It’s best to build some attraction first.

Look for Signs that She Likes You

If you are still having a bit of difficulty creating that initial attraction we recommend a few different books that can really help.

The best way to keep a woman interested is to have her interested from the beginning.

That’s why you should look for signs that she likes you already.

Does she start conversations with you?

Does she give you lengthy replies to your questions, or brief answers without following up?

Does she reply to you quickly over text?

There’s a huge difference between a 30-minute reply time and receiving a response the next day (she may be busy, but women are rarely away from their phones).

Does she send you smiley faces, and are her replies enthusiastic?

The more positive signs she gives you, the better.

It’s harder to make texting mistakes when a woman makes your job easier for you.

If she’s giving you little to work with, you’ll either have to cut your losses, or try your best to meet her in person.

The best way to make her like you is to establish a connection through real, face-to-face conversation, so meeting up with her should be your goal.

But whether you’ve met her before or not, it’s incredibly useful to know how to text older women, so let’s talk about how to actually text them.

How to Text an Older Woman You Like

The first rule to texting an older woman you’re attracted to is to avoid making a mistake in your first text.

Since we already covered the main mistakes, you know not to show her too much interest too quickly.

It’s better to start your conversations casually.

Many guys make the mistake of being too flirtatious, or giving a woman too many compliments over text.

A good rule of thumb: compliments are best when they’re given in person, and when they’re spontaneous and unplanned.

When you begin to text her, avoid complimenting her appearance.

Don’t tell her she’s pretty or beautiful just yet.

Instead, try and get her talking about herself, because the more she opens up to you the more rapport you’ll build with her.

Compliments over text are not a way to build rapport.

Oftentimes, they tell a woman that you’re just like the other guys – even if you’re not.

Moreover, allow us to give you a couple of examples of some conversations.

Try to determine why they are good (or bad) examples of texting.

 Example #1

Man: Hey Amanda how’s it going?

Woman: Hey! I’m good, how are you?

Man: I’m well. How was your weekend?

Woman: It was good. I went out Saturday, didn’t do much on Sunday.

Man: Cool. What did you do Saturday?

Woman: I went out with my friends for dinner

Man: Awesome. Where did you go?

Woman: That Italian place on Wilson St.

Man: I’ve been there before and I really liked it. By the way, are you free this week?

(no response).


If you hadn’t guessed it, this was not an example of good texting.

While he started off just fine, his texting lacked substance.

He asked too many questions to a girl that was warm at first, and cold later on.

Allowing a girl to talk about herself can only do so much.

The man also has to make her want to continue the conversation.

Let’s look at another example with better execution.

Example #2

Man: Hey Amanda how’s it going?

Woman: Hey! I’m good, how are you?

M: I’m well. How was your weekend?

W: It was good. I went out Saturday, didn’t do much on Sunday.

M: Let me guess, too many drinks on Sat, too much TV on Sun?

W: Haha no, I just went out with my friends for dinner, nothing crazy.

M: I misjudged you then. Clearly we had opposite weekends.

W: What did you do?

M: I went to my friend’s cottage. Rode a jet ski for the first time.

W: Awesome! How was it?

M: It was fun. Have you ever tried it?

W: Not yet 🙁

M: I recommend it. By the way, are you free this week?

W: I should have some time. What are you thinking?


Clearly example #2 was a much better example of how to text.

He started casually, but made sure not to get caught asking too many questions.

He teased her, by guessing the type of activities she does on her weekends.

He also gave her something to work with, by not talking about his weekend unless he was asked.

If there’s a mindset you should have when texting older women, it’s to show value, spark curiosity, and only show an appropriate amount of interest when the moment is right.

In example #2, he had her curious and asking questions.

He showed value through his fun lifestyle.

And he only asked her out when he made sure she was being responsive to him.

If there’s no initial interest, or if you fail to build it in some way, you’re unlikely to get anywhere when you make a move over text, as we saw in example #1.

Get Her Interested in You!

If there’s a final piece of advice for us to give on how to text an older woman you like, it’s to get her interested in you.

If there are no signs that she likes you yet, you have some work to do.

At the very least you have her number, which means you have a starting point.

Whether she’s a coworker, acquaintance, someone you met at a bar or through online dating is irrelevant.

Get her interested!

The second example we went through is a good frame of reference, but your own conversations will obviously be different.

Start the conversation casually.

Ask her if she has any exciting plans for the weekend.

Share something interesting with her about your plans or what you’ve been doing.

If she starts asking you questions, the conversation should flow naturally.

And remember that the best way to get her interested in you is to spend time together in person.

This is crucial if you’ve met each other online.

So talk a bit over text, and then ask about her schedule.


You: By the way, are you free this Sunday?

Her: I’m not sure yet. Why?

You: I’m usually at the coffee shop for a couple of hours. Why don’t you swing by?

Her: That’s not a bad idea. Which coffee shop?

(This is a good way to transition from a conversation to asking her out.)


One final tip when it comes to texting: sometimes less is more.

Don’t get caught in the endless cycle of back-and-forth text messaging.

Have a short chat, make sure she’s invested in the conversation, and then ask her out.

The best way to keep her interested in you is to hang out with her to solidify your interest.

Lastly, here are some more texts that you can use.

We know that it’s helpful to use proven techniques when learning how to text an older woman you like.

These can be used to ask out an older woman, or lead your texting in a positive direction.


“I have an interesting idea of what we could do later this week..” – > Follow up with a fun date idea.

“I’m going to (something exciting) this week. You should join me.”

Implying that she should join you is an interesting, and often effective way of asking a woman out.

“Do you consider yourself adventurous?” -> “I thought of something we can do together, it’s very exciting.”

This is a great way to invite her to do something out of the ordinary, like go on a hike or see a local waterfall. Try it out!


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