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How to Keep a Text an Older Woman and Keep the Conversation Going


In the world of online dating, learning how to text an older woman and keep an engaging conversation going is key. It can be a bit of an artform but the good news is, you’ve landed on the right article to help you improve your text game. We’re going to look at how to start a conversation with an older woman and how to keep it going from there. With this info in mind and a bit of practice, holding a fun and engaging conversation will become second nature.

Speaking from personal experience, I can assure you this will help your online dating so much. While you’re at it, make sure you check out our list of sites we found best for meeting older ladies to make your dating life even easier.

Where Dating Coaches Recommend You Meet Meet Older Women Online

If you've been struggling to meet older women online don't feel bad. A lot of guys are in the same boat because they use the wrong apps. Most older women are meeting guys online now, many ONLY look online. 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 Start a Conversation with an Older Woman (Online or through Text)

First things first, let’s talk about how to get a conversation going in the first place. A lot of guys find this to be the most intimidating part. You’ll be glad to hear this part is actually the easiest once you push past those nerves.

Whether through laziness or fear, the average guy does a pretty terrible job of starting a conversation with an older woman (or women in general). For you and me, that means the bar is unbelievably low — it doesn’t take much to stand out from all the noise in her inbox.

Since most of your competition tries to start the conversation with nothing more than a simple “hey” or some sleazy, recycled line, you can already start to see what I’m talking about.

Think about what you’d say if you met her on the street

Picture this. You’re standing at a traffic light downtown next to a woman and you’ve decided you’re going to talk to her. You’re not going to just say “hi” and stare at her blankly, right? That’s weird.

Instead, you’re going to mention something about her, you or the environment around you. Apply this same logic when you’re learning how to start a conversation with an older woman.

By doing this, you’ll be immediately more interesting than the endless “hi” messages she’s ignored today.

Avoid compliments about her looks

Compliments can be a great thing but they don’t often belong in a conversation starter. Sometimes it makes sense and that’s fine but you should always avoid compliments about her appearance.

Remember, mixed in with those lazy “hey” and “hi” messages are really weird, sleazy ones like “mmm, hey babe you’re sexy”. If the first thing you do is tell her how good she looks in that bikini or how beautiful her eyes are, you’re putting yourself into the same category as those creeps.

So if you think it through for a couple of minutes, you can always find something to say that doesn’t revolve around how good she looks.

New course

If you really get stuck, ask her a question

The easier it is for her to respond to a message, the more likely she is to do it. So, if you genuinely can’t think of anything right now, don’t overthink it. Instead, ask her a question about herself that she’ll find easy to answer.

Of course, bonus points for interesting and engaging questions, not “how’s it going?” or “what are you studying?”

How to Text an Older Woman

Now that we’ve covered how to start your text conversation with an older woman, let’s take a look at some simple tips to keep the conversation going. So if you’re going to use your text conversation to further the attraction, you’ll need more than just a good opener.

If you met her online, assume the interest is there or at least lukewarm if she has given you her number. If you met her through a mutual acquaintance, it should be even easier because odds are you’ve already been introduced to her in some way.

Moreover, perhaps the most important way to get started on a high note is to avoid making common texting mistakes. So let’s talk about what you should avoid in your text conversations.

Avoid making common errors

Like we covered in talking about starting an interesting conversation online with a woman, your average competition is setting the bar low. That’s great because it gives you a lot to work with — learn from their mistakes, avoid those common errors and you’re already looking great.

Sometimes, avoiding these mistakes can make the difference between keeping a woman engaged and making it so awkward she loses interest.

By far the biggest ones to look out for:

  • Texting too frequently
  • Writing too much
  • Over-complimenting
  • Seeking validation
  • Talking too much about themselves
  • Asking too many personal questions (which should be left for dates)

For instance, there’s no reason to go texting a woman multiple times every single day. Her interest will not fade if you go a day or two without messaging her — sometimes, less is truly more.

In regards to writing too much, you should aim to invest as much attention into your conversations as she does.

If she’s a bit distant, you shouldn’t be overeager.

If she’s receptive, you shouldn’t be overzealous.

Focus the conversation on her, because you’ll know she’s interested in you if she pushes questions on you.

By avoiding these pitfalls, which also include over-complimenting and seeking validation, you can move on to the following techniques in an effective manner.

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Focus on her and keep it fun

This is the one I hear my female friends complain about the most, by far. She goes on a first date with a guy, they get to chatting and almost immediately the conversation shifts to him. And it stays there. . . the entire night.

Rather than being “that guy” in your text conversation, pay attention to the balance in your conversation and keep a healthy amount of attention on her.

Ask her to tell you about herself, but be specific: “Tell me about yourself. What are you like as a person; what is your personality like?”

Keep in mind some topics to talk about over text to keep the conversation going.

You can tell how receptive she is to you based on how detailed her response is. Compliment her traits, as opposed to her looks, and be willing to share a bit about yourself if she asks.

Moreover, don’t dwell on personal questions too much. The best way to keep an older woman engaged over text is to establish fun back-and-forth banter. If you find a subject she’s enthusiastic about, stick to it to build a connection.

For example, if she says she loves traveling, ask her about the places she’s visited.

You may find that she’s excited to share travel stories with you and for obvious reasons. To keep the conversation flowing smoothly, be ready to share some of your experiences too.

Playful banter

Fun and playful banter make any conversation more interesting. The silly retorts make for an engaging back and forth which is infinitely more exciting than talking about what she’s studying right now.

The key to this is making sure it stays playful. A bit of light-hearted teasing often makes its way into this kind of banter but nobody should end the conversation feeling bad!

The way she responds in this type of conversation can tell you a lot about her personality. It can often be a good indication if she likes you over text.

Casually display your value

Since our discussion is about how to keep a text conversation going with an older woman, we must not forget the importance of establishing and maintaining attraction in her eyes.

Fortunately, attraction is not as difficult to establish as you think — If you have her number, you already have one foot in the door.

Assume that she's already interested in you and looking to take it a step further. When she asks about you, drop some fun and exciting facts about you and your lifestyle.

If you play an interesting sport or have a unique hobby, be sure to mention it. Instead of just dwelling on your job, talk about some of your most memorable experiences – and ask about hers in return.

Remember, you’re only talking about yourself because she asked, and you should lean towards hearing more about her.

In addition, if you’re using online dating, make sure that your photos are top-notch. Invest in professional pictures because they make a significant difference.

Instead of writing a long-winded profile description, keep it as concise as possible. Focus on having several excellent pictures that showcase your value instead. Be seen as an interesting man that does interesting things, and most of all, lives an interesting lifestyle.

It makes sense, right? Interesting people are way more fun to be around. Just don’t let this turn into a bragging session, that’ll have the opposite result.

Build rapport and have a purpose when you text an older woman

The final point to cover on how to keep a text conversation going involves building rapport and having a purpose behind your messages. That purpose is primarily flirting with her through text.

Ideally you’ll establish some attraction and perhaps even build on it as your conversation progresses. Since neither of you are looking for a penpal, your goal should be to see her on a date —  the best connections are made in person.

Move towards asking her out if you haven’t already. Find out when she’s free.

A great way to ask her out: “You seem interesting. Do you have some free time this week? We should meet.”

If you’ve built that rapport and she’s genuinely interested in you, there’s a very good chance the two of you will be meeting up soon.

Fortunately, rapport is easy to build if she’s already interested. As long as you don’t rush in asking her out, you’ll be fine. By following your gut and the points we’ve just covered, you’ll naturally create rapport with her through text.

There’s always work to do, but keeping a conversation going with an attractive older woman after starting from scratch, and managing to see her on a date is an achievement in itself.

When you do see her, make sure you maintain the playful and intriguing vibe you’ve presented, and you’ll do just fine.

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How to Message an Older Woman Online

The advice in this article so far can be applied to both texting older women and messaging them online. Before we wrap up though, I wanted to cover a few quick tips specific to online dating.

Pay attention to her profile

If you’re starting the conversation on a dating app or website, you have the luxury of time and her carefully curated profile. Whether we want to admit it or not, we all spend time crafting a profile that demonstrates who we are.

For you, that’s ideal because it gives you a glimpse at her personality and what she enjoys. Yoga photos? Running? Skydiving? Puppies? Photos at the Louis Vuitton store? Maybe she has a vacation photo from somewhere you recognize.

If you look close enough, you’ll find at least five different things you can message her about from her profile alone.

Be quick to escalate

Once you’re comfortable with how to message an older woman online, you’ll get a feel for how interested she is, early in the conversation. If there’s mutual interest and you’ve built some comfort, go ahead and give her your phone number.

If you feel like things are going well after 30 minutes, why spend three days messaging back and forth on the dating app? Give her your number to text you and move your conversation to the next stage.

If she does send you a text, you know she’s into you and wants to see where things go.

Check your expectations when you text an older woman

This is as much for your sake as hers, honestly. I’m a big fan of online dating but a common mistake I see my friends make is expecting something from every conversation.

That’s just now how dating apps or websites function at all. At this early stage of the conversation, neither of you owe each other anything. If she’s not feeling it, she may just stop replying and in the culture of these platforms, that’s perfectly fine.

Don’t go triple-texting to get a response or getting frustrated because you “deserve” a reply. Try to learn what you can from the conversation and move on.


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