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


With so much of modern dating happening online, knowing how to text an older woman you like is an important skill. It can feel a little intimidating to start, but with a few helpful tips and some practice, it’ll become second nature.

That’s exactly what we’re going to look at in more detail today. The more you understand what to avoid and the right mindset, the rest will follow quickly.

The Best Dating Apps to Meet Older Women
(According to Dating Coaches)

Whether you want to practice texting older women or you want to get better results you need to be on at least one dating app. Most older women are meeting guys online now, many ONLY look online. There are a lot of apps out there but not many are great for meeting single older women. These are the best options right now that consistently work for regular guys:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Decent For Younger Guys
Cougar Life Highlights
Cougar Life Highlights
  • Focused on younger men meeting older women
  • A mix of relationships and hookups
  • Growing
  • Not as popular as eHarmony of AFF
Try Cougar Life

How to Text an Older Woman You Like

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

Firstly, allow us to point out the mistakes you should avoid. These are mistakes you want to stay away from whether you met on the street, online, or the few truly great places to meet single 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. If you’re chatting online or you just recently met her, you have to be more careful to avoid a mistake that might ruin your chances.

One immediate texting mistake we must mention is texting too much. Texting 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.

Instead of long and constant messages, look for quality over quantity. Shorter, more engaging conversation will help you stand out from the crowd. Instead of talking about the weather outside, ask about her weekend. Also, follow up with questions about what she enjoys doing and get to know her better.

This makes for far more interesting conversation and keeps things from becoming one-sided.

Look for signs that she likes you

If you’re still having 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 engaged 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? And 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.

Does she send you smiley faces, and are her replies enthusiastic? The more positive signs she gives you, the better.

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.

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

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How to text an older woman you like

When starting the conversation with her it’s important to kick things off on the right foot. Aim for casual, low-effort conversation and go from there to keep the text conversation going. Jumping straight in with heavy flirting or sexual comments sets the wrong tone and isn’t likely to end well.

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.

Let’s take a look at a few examples here.  Which do you think are good examples?

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 a bad example of how to text an older woman you like. While he started off just fine, his texting lacked substance.

He asked too many questions to a woman who was warm at first, and cold later on. Allowing her to talk about herself can only do so much. The man also has to make her want to continue the conversation. So always have some good topics to talk about over text!

Single woman

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. Also 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.

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

In example #2, he had her curious and asking questions. He showed value through his fun lifestyle rather than asking mundane questions in rapid-fire.

Also important: 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. Build rapport, take an interest in her and demonstrate the type of person you are. Most importantly, flirt with her over text and see if there's some chemistry there.

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.

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.

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.

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Another example of how to text an older woman you like

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


“I have an interesting idea for what we could do later this week..” - > Then 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. Follow these tips and it will only be a matter of time before you start wondering what to text her before the first date!

When texting an older woman you like, make sure you focus on building a connection. It's not all a matter of sending compliments, flirtatious texts and sexual innuendos. Take it slow, stimulate her mind and see how she responds. If she reponds positively, you're on the right track, so keep going!


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