Ask the Dating Coach Blog

Adam Lyons Dating Advice

The Best Way To Keep A Text Conversation Interesting

3 min read

?ouple cuddling and kiss in kitchen. side view

I have a surefire way to make sure your text conversation is interesting… Have you ever been in a conversation with someone, maybe on a dating app, but you’re worried that the conversation isn’t going anywhere? That can lead to confusion and panic. 

I’m going to give you a very fun game that not only lends itself to a great texting conversation that goes on for a very, very long time, but also teaches you so much about the other person.

Better yet, it almost always turns into a more adult and intimate conversation. 

How to Gamify to keep your text conversation interesting

It happens after about the second or third message. You can say the following:

Have you ever played 20 questions?

The other person might say yes, or they might say no. Either way, you can say:

Here’s how it’s going to work. I am going to send you a question. You send an answer and then I’m going to answer the exact same question. After that, it’s your turn to ask a question; I’m going to answer it and then you answer it. 

You’ll ask 10 questions each, but both of you need to answer each question. 

What’s great about this is that this conversation is more fun than just trying to be like, “Hey, so what’d you do for fun? Where are you going?” 

interesting text conversation

Differentiate yourself to keep them interested in the conversation

We want to have a conversation that is different than the kind of conversation that everybody else is going to have. 

The whole goal is to make you stand out because there’s going to be countless other people communicating with them. We need you to be the most fun. 

Now, the cool thing about 20 questions is people run out of questions and they get very bored. When they start running out of questions, the questions tend to get more intimate. You’re going to want to make sure that at about question four, you’re asking somebody:

When did you have your first kiss?

Now that particular question is the most important question. So you’ve both traded a couple of questions and then once it gets back to you, you’re going to say:

Okay, when did you have your first kiss? 

Now what’s great about this is we’ve just shifted the entire interaction. It’s playful because you know, it’s PG-13, but we’ve definitely shifted into talking about relationships. It is very, very rare after that if the conversation doesn’t turn to somewhat of a sexual nature.

The topics might become more about the weirdest place you’ve ever had sex. How old you were when you lost your virginity, et cetera, et cetera. 20 Questions is a great game to play. It keeps that conversation going, it will almost always turn to an intimate nature, which makes dating that much easier.

Watch Adam explain how to play 20 questions and keep the text conversations you’re having interesting:

If you missed yesterday’s post on how to get her to send you nudes read that next!

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