5 Things To Talk About Over Text With An Older Woman To Keep Her Interested​

With these five things to talk about over text, you'll keep the conversation flowing.

Texting is the new form of communication, especially in the dating world. Whether it be on one of the top cougar dating sites or after you’ve already gotten the ball rolling, being able to keep an older woman interested is vitally important to landing a date and hopefully more. So what are some things to talk about over text?

The best things to talk about over text

One thing to note is older women are not much into texting as younger women. It’s one of those things they got caught up in as trans-generational adults.  

So getting an older woman interested in texting you continuously might be a little bit difficult — not because they are not interested in you — it’s just not their thing. By being creative, however, you can really keep them glued to their devices waiting for your next text.

That’s what this particular article is all about — teaching you how to be creative and crafty with your text so that women respond to it . . . and quickly too.

If you still feel like you are struggling with your overall approach to dating there are a few books worth checking out that can really help.

1) Something That Made You Think Of Her

A good conversation starter with an older woman is telling her of something that made you thought of her during the day.

If you see a poster or heard someone talking that reminds you of her, then text her and tell her about it. This is way better than the “hey” texting starter. It shows that you often think about her and she’ll be really flattered.

Most older women find this to be really romantic and I think it is. It tends to touch a chord within our heart when someone says they were or are thinking about us and how much more by proving it? By associating an event or a person with what you texted her, you were able to prove to her that you were actually thinking about her and not faking it just to get her in your bed.

Try keeping this simple and light.

2) Jokes Are One Of The Best Things To Talk About Over Text

Women generally love to laugh. Not only women — We all love anyone that can make us crack up easily. We like associating with them.

The same with older women. They want someone that can easily add fun to their already hectic life and if you could be that person then they will want to draw closer to you.

You don’t have to be the funniest person around to text a joke. There are lots of jokes that you can send to her that will make her crack up. Google is there to help you.

A joke that makes you laugh will probably also make her laugh. Let the joke be centered around everyday things people do as everyone can easily relate to this. Avoid lewd jokes except you have gotten to know much about her and that she’s OK with those coming from you or else keep it out.

3) Poems Can Be A Great Way To Show Your Sophisticated Side

Why prove your love the same boring ‘I love you’ or ‘I miss you’ ways as most other guys? You can make yours even more memorable and romantic. A simple poem about her is a very great way to make her feel special and know that you have more feelings for her than getting in between her legs.

The poem should be very personal. Writing this sort of poem is not very hard. Think of how you feel about her, her personality, her eyes, hair and so on and try to describe them with romantic words.

There are plenty of romantic poems on the internet. If you find it hard scribbling a romantic poem then you can search the internet, get one and tweak it to suit her personality.

Poetry is a great way of getting an older woman interested in messaging you. It shows her that you’re willing to sacrifice your time and use it to actually think about her and construct a beautiful description of her. This is a very powerful weapon that you might want to include in your texting.

4) Remember The Details

Most guys have many things they can talk about over text with an older woman if they will only pay attention to details. You don’t have to come up with a new topic each time you want to message her — that makes both of you like strangers again.

Try building connections with her by going back over previous chats and ask her a few questions about it. It may be something you want to know more about or are confused about. Feel free to ask her again the next time you’re texting her.

Including the details of your previous conversation is also a good way to show that you’re actually listening to her.

Did she tell you that she was going to the vet with her pet during your previous texting session? You’d do well to ask her how the meeting went. This translates that you actually care about her and her everyday life.

She’ll appreciate this more than starting a new topic without reference to the previous text.

5) Her Profile Is A Key To Finding Things To Talk About Over Text

Profiles on most social media and dating sites provide more details about an individual than we can actually gather by talking with them. This is all available at your fingertips.

Before messaging a woman, you might want to check her profile and see her likes and preferences.

Once, I met a great looking woman on Facebook. She was three years older than me and had two kids – 2 boys actually. She loves playing golf and likes camping, and found Mr. Bean hilarious.

I could have started a conversation with her on any of these but something else actually caught my attention – a lyric from a popular rapper. I couldn’t believe this so I texted her if she’s a fan of that musician and she was. With that, we played a little ‘don’t forget the lyrics’ game like old friends.

Before texting an older woman for the first time, or even if you’ve both been texting, you might want to visit her profile. Check her pictures to see if she’s interested in pets or engaging in any hobby and message her about it. Most women will respond to these texts instantly because we all love and want to associate with people who enjoy the same things as us.

Bonus Tip:

As a bonus tip — Keep your tip in your pants. You’re trying to be interesting and that means separating yourself from the rest of the messages she’s likely getting. That means keeping it tucked away until it’s time to use it.


Everything takes practice before one can become perfect, so you might want to take a few moments and practice a little mock texting before actually sending her a message.

Keep the mock-texting quite simple. You can practice this with your buddy. Or better still, you can do this alone by taking a few minutes to think of all the possible responses she might give to your texts and what to say to each in other to keep the conversation going.

Don’t be too rigid, try being in the moment. Many guys often ignore this all-important step and make the very big mistake of texting the very first thing that pops into their minds.

Older women are no longer girls that can easily be swayed by lewd jokes or sweet compliments — though it can still sway them — it must be well articulated and few guys can actually pull this off. They desire maturity in a younger man and if they find it, they’d do almost anything to get that guy.

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