9 Simple Ways To Keep A Conversation Going Over Text

You’re texting someone you like, but you’re worried that the conversation is getting a little boring.

So you’re wondering how to keep a conversation going over text.

After reading this article, you’ll find it easy to keep the conversation fun over text.

This is what you get:

In this article:More...

1. Avoid serious questions

Many people make the same mistake when texting someone they like:

They try to keep the conversation going by asking serious questions.

Let me show you an example.

So got any plans for the

Probably going out and see
some friends

That’s great

Any cool bars you recommend?

Anything busy in the city center

I see

What are you up to right now?

Annnnnd… She doesn’t respond.

Why did she stop texting?

I get why men ask a lot of questions, but here’s the problem. You want her to feel excited when texting you, not just have a plain conversation.

Find out in the next tips how to change this around.

If you want to know if you’re texting all wrong, check out this article:

2. Turn your questions into assumptions

Let’s say you’re texting your crush, or a girl on Tinder. You’ve exchanged a few texts, and suddenly you’re thinking of asking a question:

“Do you have any siblings?”

Before you type out that question on your phone, take a moment to answer it yourself. In other words, make an assumption about her.

I have a feeling you’re an
only child

Haha, what do you mean?

I just think you got a lot of
attention as a kid 😉


Is that good or bad?

I actually have just an older

Do you see the power of assumptions? Instead of just asking her a question, you’re giving value by offering your perspective.

And that’s great, because:

  • It’s unique (it’s your point of view, and she probably hasn’t heard anything like it before).
  • It’s relevant (you’re talking about her).
  • It’s easy for her to respond to.

Not only will she be more interested in someone who can do these things. But you can also keep the conversation going as long as you want, because it’s based on your own assumptions. Assumptions that never run out.

So, if you become skilled at making assumptions, you’ll never run out of things to say.

Also, check out this article:

3. Spike her curiosity

If your texts are boring, she might not feel like replying.

But how can you write a text that makes her want to respond? Even better, how can you write an irresistible message?

It’s a bit like those catchy titles you see on YouTube: ‘1$ versus $100,000 Plane Ticket!’

You can use the psychology of curiosity by sending a text like:

  • I had a funny thought about you…
  • Haha you passed by in my dream tonight
  • Do you know what’s interesting about you?

Great example texts. But what do you say after that?

I’ve done all the hard work and created the most effective opening message ever.

It doesn’t matter who she is; my text is irresistible to every girl on the planet.

Grab it here for free and try it out.

And also get a video of me explaining how to continue the conversation with real examples.

4. Share cool stuff from other people

Here’s a super easy trick for you.

Borrow content.

With the right stuff, you won’t even need to write a lot of words. But before I show you what I mean, remember this important rule:

  • If the video you’re sharing is longer than 20 seconds, it’s too long! Skip it.

If she’s like most of us, she spends a lot of time learning and working.

So if she opens her Instagram / iMessage / WhatsApp, and sees a super long video, she probably won’t watch it.

But if you keep it short, she’ll quickly watch your video, just like eating an M&M, and then she’ll text back with a smile.

Content that is always great is anything with animals.

This is us in 10 years

I’ll give you another joke to keep the conversation going in a flirty way:

omg. Just found one of my childhood drawings

Really, really easy. And it usually keeps the conversation going because it’s so much fun.

Who wouldn’t enjoy getting small, fun bits of content?

So here’s my tip for you: Whenever you find a meme or video that makes you giggle, send it to the girl you’re texting.

5. Understand her better

Whether you’re texting your crush or someone on a dating app, it’s important to understand the other person.

So when you text her for the first time, or you ask her a question, think to yourself:

“Has she heard this more often? How does this text make her feel?”

A great example of this is women with a certain name:

First, he sets her up:

How many pickup lines do you get with the name Destiny

She answers, “TOO f’n many”. (As this guy assumed correctly.)

Next, he adds some self-deprecating humor using the Pendulum Effect. This means he takes a risk and swings the pendulum to a big exaggeration.


“Louis, I get what you’re saying. But I don’t think I could write such a crazy line without lots of thinking.”

That’s fine. Being witty takes practice.

My advice to you is: try out the personalized opener to develop your text muscles and if you can’t come up with anything good, use my clickbait opener.

Want more ideas on what to send to a girl? Check out this article:

6. Use free association

Sometimes a girl will shoot you a text and you just don’t know how to reply.

Which is fine. That happens to all of us. Especially if she’s not giving you much to work with.

The problem is, when you’re not sure what to say, you might end up saying something not very interesting. It might be a boring question.

But here’s a simple way to keep the conversation going without asking questions.

I’ll show you with an example from one of my clients in the TextGod Mentoring Program, where he used her bio:

I just came out a terrible relationship, so please bear with me.

A clever pun that got him some attention. But now my student faced a problem – he didn’t know how to keep the conversation going.

So I shared with him my favorite method for continuing a conversation:

Holding onto the same topic.

This means you stay on the same subject while making it enjoyable. To keep it fun, I use a technique called free association.

Here’s my next message:

You can find me at the monkey bars with a bag of bananas

But I don’t stop there. Because that text alone might not be enough to help her respond.

So I add another little message:

Also, there was a time where I ate 18 kgs of bananas a month

I add that last line because it’s likely to get a response from her.

And if she replies, I’d keep the conversation going by continuing on the same topic, something like:

Nah, j/k. But I do seriously have a friend who is half human/half orangutan

By now, we’ve pretty much talked about the ‘monkey’ topic. So I’d use my second technique to keep the conversation going.

For more texts to send after a boring text from her, check out this article:

7. Use value-giving texts

Repeatedly asking questions is a bad idea because it screams neediness:  “Uhh… uh… Here’s a quick question so I can hold your attention for a few more seconds!”

So what type of text is the opposite of needy?

A simple value-giving text.

That description obviously gives you no direction. So let me give you some extra guidelines.

Share a personal highlight.

My go-to value-giving text of today is:

Just woke up after I had my first jiu jitsu lesson

Still shaped like a pretzel

Put simply, it’s a change in the conversational direction that also offers enough info for her to come up with a reply. Probably something on sports and/or working out.

The key point I want you to remember is:

Whatever experience you share, make sure to write it in a way that triggers emotions.

Looking back at my jiu jitsu text, I ended on the punchline:

“Still shaped like a pretzel.”

Depending on your text, your emotion-triggering device could be:

  • A joke.
  • A funny word.
  • A funny/noteworthy experience.

As long as your conversational change of direction stimulates emotions, she’ll answer and you’ll keep the conversation going.

Want to make her feel more and laugh over text, check out this article:

8. Voice your opinion

Let me give you a great non-needy way to keep the conversation going.

Voice your opinion!

Here’s an example from Tinder:

Thanks to today’s culture, she’s doing some serious explaining in her bio about politics.

Fair enough. Because to some people, her flag swinging will be misinterpreted.

Anyway, I think it’s a shame that she’s explaining herself.

So that’s what I told her:

And she loved it, but I didn’t love her answer:

So what did I do?

I went against the flow and tease on her follow-up text:

How do you think she replied?

See for yourself:

  • She laughed
  • She sent three messages
  • She tried to convince me she was ‘pretty far from generic’


That said, in this case I took a risk and it paid off. While most women appreciate it when a man voices his opinion, nobody likes to be insulted. And calling someone ‘generic’ will quickly fall into the insult category.

So if you do speak your opinion and go against the flow, try and be respectful.

9. Flirt with her

Now for one more method to keep the conversation flowing. Probably the best method of all.

Not just because it moves the convo forward, but because this method gets you closer to your goal: setting up the date.

The one thing we’ve been circling around this entire article….


Which goes far beyond showing interest in someone.

For those who don’t have the definition at the ready, Google says:

“Behaving as though sexually attracted to someone, but playfully rather than with serious intentions.”

That’s quite a mouthful. So here’s a simplification:

Flirting = showing interest + being a challenge

And if you flirt right, you create attraction right off the bat. Here’s the difference between being too normal (read: boring):

Hey, how are you?

Hey! Super good!


And flirting:

Hey, how are you?

Just came back from a walk.
Saw the cutest puppy of my life.

And you didn’t snap a pic
for me? 🙁

Haha I’m sorry, I have a new
crush now and it walks on all fours

Holy Tip:

Do not make the mistake of flirting with a girl when the conversation is dying down.

I understand the urge. Flirting usually does a great job of making a girl feel good and capturing her attention.

But flirting is also a gift. And if she’s acting in a way that isn’t worthy of praise, like if she’s sending short texts and replying slowly, flirting with her is low-value behavior.

It’ll just make her think, “He’s so desperate for my attention even though I’m not being nice… Can’t he take a hint?”

So if she’s not putting a whole lot of effort into her texts, you’re best off…

Teasing her!

Find out how here.

Keeping a conversation going over text – Summary

The key to keeping conversations going over text is a lighthearted vibe. Online chats aren’t about delving too deep. That’s for when you’re face-to-face. Text exchanges are all about maintaining emotional momentum and setting up dates.

That’s why you want to focus on keeping your conversations fun and easy to reply to. Such as by sending fun memes, sharing highlights of your day, teasing and challenging her, and being curious. Just as we discussed in the tips above.

This is basically all you need to know on how to keep a conversation going over text.

For more help, click the big button below to get my 10 texts that work in any situation + my most powerful texting technique of all, The Personality Slice.

Enjoy, brother.

Louis Farfields

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  • Max says:

    Tinder doesn’t allow sending videos directly, does it? Has to be done sharing the link to YouTube, or I there a secret technique I’m missing out?

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