When you’re texting with someone you like, do you struggle to know what to say next? Or maybe it feels like you’re in a texting rut, and keep having the same conversations . . .

Today’s video is a mini toolkit for these exact situations, with 17 high-value texting suggestions that restart attraction, lead to a date, or just bring you more emotional connection. 

Use these practical messages to inspire better communication in any dating situation!

---

Craving Conversation

You send him a message that says, “I’m craving our conversation.”

Here’s what this message does: you’ve snuck into his day and jolted him out of whatever he’s doing right now, to bring him into the moment with you. It wasn’t small talk: “Hey, how you doing? What you up to? How’s your day going?”

You just jump straight into something meaningful, and you’ve paid a unique compliment to the dynamic you have with him.

Be Adorably Demanding

“Ahem. Why haven’t you asked me to see the new ‘Blade Runner’ yet?”

This message is adorably demanding in a playful way. It’s vulnerable on one hand. You are saying, “I want to do this with you.” But it’s also slightly unreasonable because he didn’t even necessarily know that you wanted to see that film. In fact, I would say this message works better if he didn’t know you wanted to do that thing. And you’re being up front about what you want. You’re putting the ball in his court and saying, “Hey, Mister, invite me on this date please.”

5 Texting Mistakes
Playing Games About When to Text Back

Now, let’s say Monkey receives a text. Is from George. But instead of texting George back and having a conversation, Monkey thinks: “No, I am going to wait. And George is gonna see how busy I am, how important I am, and how attractive I am.”

But the problem is, George is by his phone RIGHT NOW. She could have had a message with him and carried on the momentum and ridden that wave. Instead, she waited five or six hours to text back George, who incidentally, was no longer curious.

Now look, I’m not saying that when someone texts you, you should always be by your phone waiting to text them back. But if someone happens to text you in a moment where you’re not doing anything, and it’s organic to reply to them right away, why not use the momentum of that moment and have a conversation? If 5, 10 minutes later you need to go, that’s fine. That’s where you can be busy in an authentic way. But don’t play the game of making someone wait just to look cool.

Obsessively Sticking to Text as the Form of Communication

I think of different mediums: whether they’re texts, pictures, voice memos, phone calls, FaceTimes, as all having a kind of energy bar. And the more you do them, the more that energy bar gets depleted, and we start to get diminishing returns from that thing.

If we over-text, it doesn’t matter how quirky or fun or witty we are by text, it begins to wear thin, and most people have had that experience. It’s like, okay, I need different stimuli now. I need something else.

That’s when it pays to send someone a picture and just say, “The view from where I am right now,” if you happen to be looking out at a beautiful view. Or if you happen to be sitting in bed with a dessert in front of the TV, take a picture of the dessert and be like, “My view right now.” In that moment, you’re changing up the medium.

The same can be done with a voice memo. In the middle of a text conversation when you feel like it’s getting a little dry, send someone a voice memo instead. If they’re teasing you, shake it up by sending a voice memo back saying: “You’re so mean.” It’s cute. It’s playful. But it’s a pattern break that suddenly injects new life into the conversation because the energy bar is not depleted.

Being One-Note

What gets someone really attracted to us is not when we’re one energy, but when we’re able to be versatile between different energies. If you find yourself always being very polite and sweet, today be a little bossy. Say to someone: “Are you going to call me tonight or what?”

If you find yourself sending lots of nice, friendly messages to someone, amp up the sexual tension today. Tell him: “You looked really hot in that picture you posted today.”

Those are things that show that you can be many things. So think of the energy you normally have—the one you’re most comfortable with—and do the inverse of that today.

Talking About Everything Except Yourself

People truly fall for you when they hear your story, because your story is what makes you different from everybody else. So the next time you have a conversation with someone, ask yourself this: “Am I only describing here what I’ve been doing? Or am I actually revealing who I am and what I’m thinking about?”

Here’s an example because I know this sounds a little abstract: If someone asks you “What did you do last night?” you may say, “I cooked ribs for the first time last night.”

Now, that’s not a bad text—it’s still a conversation starter—but it’s still only talking about what you did. What we want to do is add on to that a bit about who you are. If you wanted to do even better than that in telling your story, you could say, “I made ribs for the first time for my family last night. I’m a little late to this cooking thing to be honest, but I’m actually really enjoying learning about it.” Now someone sees a hint of vulnerability, what you’re learning about right now, and how you feel about it.

Being Too Passive

Almost everybody has had the experience of something moving way too slowly—of someone who keeps drifting back and forth, giving you kind of mixed signals. They’re not asking you out, but they do keep reaching out by text. You don’t know where it’s going; it feels totally ambiguous. This is where I like to apply what I call gracious impatience, which means warmly, politely being more up front about what you actually want.

So let’s say Monkey wants to progress things with George. Now, they’ve been texting back and forth for a few weeks, but it seems like the momentum isn’t carrying them to the next stage. She’s thinking: “Why doesn’t he ask me out on a date? Why doesn’t he at least pick up the phone? Here I am just texting away. Am I going to text myself into an early shallow monkey grave?”

Well, the passive response would be to keep texting George and be like, “Yes, I think that that is true as well, George. Bye, George. We’ll do the same thing again tomorrow.”

Or Monkey can be graciously impatient. The next time George messages her, she can say, “Yeah, that’s a real funny joke, George. You’re a real funny guy there. So, anyway, Mister, are you actually going to ask me out? Or can I just expect a ‘How’s your week?’ for the rest of my life?”

Now, I know this sounds like a simple message, but there is a lot that is right with it. When you say “So, anyway, Mister,” there’s a little bit of an authoritative, almost sexy tone to that. You’re being demanding, you’re being a little bossy. Then you give the standard: “Are you gonna ask me out?” that’s what you want. You’re actually saying what you want. And with: “Can I just expect a ‘How’s your week?’ for the rest of my life?” that’s you being intentionally hyperbolic and dramatic to create a playfulness around something that you’re also kind of not playing about.

People can have a hard time getting momentum—from a first conversation to FaceTime or an actual date, or from date one to date two—or they had momentum and they lost it and they don’t know how to get it back again with that person.

I wanted to create something that showed people how to get momentum in the early stages of dating someone, and then keep it so that it actually turned into a relationship. And the way that I’ve chosen to do that is to create a texting program that shows you—I think there’s like 60 or 70 different text messages in the program that you can use to create, to sustain, or to regain momentum with the person you’re dating. And I did something even more unique because I created a numbering system whereby it goes from one to five—number one being you just met this person, and it’s the very first message. And number five being you actually feel seriously about this person.

And I assigned each one of the text messages I give you in the program a number so that you know when to send the message and when not to send the message. I’ve called it The Momentum Texts. I’m very proud of it. It’s like a cool little program. It’s not a big program. It’s really quick to digest. It’s the price of two lattes, or one and a half lattes if you live in Los Angeles. Go check it out at MomentumTexts.com. I’ll see you there.

Case Study: Creating a Deeper Connection

Recently, I was coaching a woman who showed me a text exchange with someone she had met on an app. The exchange went like this:

She said: “Hmm, are you just a flirt? Or is there more to you?”

He said: “Are you just a Debbie Downer? Or more to you?”

She said: “You have to be more than a flirt to find out.”

He said: “You’re a lot to deal with.”

Although that guy sounds like kind of a jerk, and probably not someone she wants the attention of, there is something that she said that I wanted to pick up on. She said, “Hmm, are you just a flirt? Or is there more to you?”

Now, the problem I have with that is the intention is good. What she wants to see is if this exchange can become more than a flirtatious or perhaps even a sexual interaction and become a deeper connection.

I believe the best way to do that is not to ask, “Is there more to you,” but to show there’s more to YOU. Because when you reveal more about yourself, what you’re really saying to someone is, “Here’s me. Can you be that too?”

I’ll give you an example: Let’s say a guy texted a woman and said: “What are you up to?” Now, she could just give a plain response: “I’m with my family right now. What’s going on with you?”

Or she could see this very simple question as a way to tell her story and reveal more about herself. So he says, “What are you up to?” She says, “I’m building a desk from IKEA with my dad and my sister and none of us seem to be able to do it. So we’re just rolling around on the floor laughing instead.”

Now when that woman says that, she’s revealing a lot about herself. She’s a family person. She has an adorable, affectionate relationship with those members of her family, in this case, her dad and her sister. She’s self-deprecating, and can laugh at herself in a situation. All of that is telling her story.

Now, that does something very subtle. It shows her in three dimensions, and the effect it has is that it invites him to either show himself in three dimensions by getting vulnerable in return and revealing more about his life, or, at the very least, it invites him to recognize her in three dimensions—to see her as a more rounded, real human being to invest in.

Now, if at this point, he doesn’t do either of those two things and instead, he just says, “So what are you wearing while you’re making the desk?” he’s showing that he is either completely one-dimensional, or that his intentions are completely one-dimensional. You learn more by revealing your own self and your own story than you do by asking someone to reveal theirs, because everything is shown in their reaction to you opening up.

Add a Human Detail to Your Text Messages

It’s one thing for someone to say, “How’s your day going?” And you say, “It’s going well, thanks, how’s yours?” It’s another thing to say, “It’s going well. I’m about to go on a run.”

That gives someone a detail, something they can craft a conversation out of. Or you could go one step further and say, “It’s going well, thanks. I’m about to go on a run. I’m dragging my little brother with me.”

That now gives them a human detail on top of it—something that paints a more three-dimensional picture of you. In a world that’s 2D, we have to make ourselves 3D.

Shorten the Timeframe

If you’re talking to someone on a Monday, and they happen to be leaving the conversation to go into a meeting, don’t finish that little chapter of the conversation by saying, “Have a great week.” Say, “Have a great meeting.” That’s an interesting phrase. Or say, “Have a great workout,” or “Have a great [whatever they’re doing right now].”

Because it’s something you send to someone you actually know. You may have only met this person yesterday, but when you say, “Have a great meeting,” there’s something familiar about that. There’s something personal about that. There’s something that recognizes what they’re doing right now. And it also makes it easier to pick up the conversation by them telling you how the meeting went, or by you asking how the meeting went. “Have a great week,” says, “I’ll talk to you next week.” But “Have a great meeting” says, “We’ll talk later today.”

Create a Shared Reference Together

If someone tells you something like their favorite TV show is Ted Lasso . . .

Ted Lasso’s voice:
“In a matter of minutes, your relationship dilemma will be in the past.”

Matthew:
Then the next time you have a moment of banter, fun conversation, find a GIF that fits what you’re talking about from Ted Lasso.

Ted Lasso’s voice:
“If that’s a joke, I love it.”

Matthew:
That then creates this moment of:

A) I know you a little bit.
B) I was listening.
C) We now have a shared reference together—something that builds our story.

Side note, when you send a GIF, it’s a form of pattern break in a conversation. So it’s been text, text, text, text, text, and then this GIF comes through. And it’s just like this little moment of animation. It doesn’t have to be a GIF. It could be a voice note, it could be a picture. But when you do something like that, it’s a pattern break that grabs someone’s attention.

The Intrigue Compliment

Give someone a compliment that’s specific, but begin it with this phrase: “Do you know what I like about you?”

First, you’re signaling that something interesting is coming. How do I know it’s interesting? Because it’s about them. And that’s the most interesting subject in the world to that person, right? So: “Do you know what I like about you?” Pause, right?

You can do this in conversation too and just take a beat. But in text you say: “Do you know what I like about you?” And then you can wait for them to respond, or just take a few seconds or a minute and then send the next part. That creates this moment of suspense, intrigue, curiosity. And it then allows you to give a specific compliment that shows not only a generous nature, but it also shows confidence, because you’re confident enough to actually embrace and speak out loud about something specific you like about another person.

The Accelerator Text

The idea behind this message is just to keep things moving. We have to have an unwillingness to stand still—an unwillingness to be in a situation where there is no momentum. And that means if you keep getting texts from someone that don’t go anywhere . . . someone keeps sending you superficial details of their day or what they’re up to, asking how you are, but never culminates in a date, you have to have a low tolerance for things that don’t go anywhere.

We had this example a week ago where someone said: “This guy, he’ll literally text me and he’ll tell me he’s making soup. But he never asks me on a date, but he’s the one who proactively texts me.”

So here’s what you do: You ask him what soup he’s making. He says, “Chicken soup.” You then say, “You know what’s even more fun than chicken soup? Chicken soup on a date.”

And you see what he says to that. That’s you calling him out for the fact that he hasn’t asked you on a date. It’s firmly putting the ball in his court and saying, “Your turn.” That may be playful—it’s not aggressive—but it shows an unwillingness to ignore the fact that right now, this isn’t progressing.

The Twilight Phone

Voiceover:
You just crossed over into the Twilight Phone.

Matthew:
Our story begins with a friend of mine, who met a guy on a Friday night. What you’re about to see is a real text exchange between this man and her that started on Sunday.

He sent her a message saying: “Great meeting you.”

She then said: “You too. How’s your Sunday been?”

Pretty decent start, right? Except for the fact that he didn’t reply. Until . . .

“Well, Tuesday has been great. How’s your week been so far?”

She then replies: “Haha. You reply at grandpa-esque texting speeds.”

Now, I actually like this message. I like the fact that she’s calling him out on how slow he is at texting. What I don’t like is the little “Haha,” where she softens the blow in the beginning. I kind of want her to just say it without even worrying about offending him in this moment.

She then says this: “Really good week. About to get really crazy though.”

Now, I would have been happy if she just left it there. I know she’s not asking him a question, and that might seem like the polite thing to do, but this isn’t about politeness. It’s about attraction. And in this moment, he might have just been messaging her because he’s bored. To prove that he’s not just bored, she should allow him to do a little more work. Instead, here’s where it goes wrong:

“Which is why tomorrow I could do with getting a happy hour drink with a handsome gentleman. 7 p.m.-ish?”

Here she does all his work for him. Now, if you know my philosophy, you know I don’t have a problem with a woman asking a guy on a date. But in this scenario, he has not earned this. All he’s done is send a low-investment message. So I wish that she had allowed him to get himself to that point, instead of rushing to arrange a date based on two messages.

And here’s how you know she went wrong: He didn’t text her back on Tuesday. He didn’t even text her back on Wednesday. He didn’t even text her back on Thursday. He didn’t text her until . . .

Do you want to know what he sent? Grandpa emoji.

Now the fact that he sent this emoji of this poor old man doesn’t make him a bad guy. It just makes him a guy who’s not trying very hard right now. And as you know, I’m always encouraging women to give investment to men who are investing in them. And to her credit, knowing what I would advise her to do in such a situation, my friend didn’t reply, which brings us to . . .

Now, it’s almost as though between Friday and Tuesday, he realized, “Uh-oh, I may have screwed this up.” So he gives his reasons for not texting back quickly enough: “I mean, it’s just that my wifi is slow. My phone wasn’t working. I dropped it and it was dunzo. Last week was a crazy busy week. And also, I’m really slow when it comes to texting.”

Now, this is where my friend came to me two hours after she had received that message. She said: “What do I text back to this guy?”

Now, my first question was: “Do you actually want to see this person again?” To which her reply was, “Yes.”

For those of you watching out there who say, “I wouldn’t want to see him again,” fine. That would be your decision. For her, she did want to see him again. So I said, “Give me the phone.” She passed me the phone, I wrote out a message, and hit send. And it was a very different message than the one she would have sent:

“All good. Have a great week.”

Now, why did I send this? Because in this moment, he’s expecting to give a bunch of excuses and for her to take all of that rationale on and say, “Oh, it’s okay. No worries, how’s your week going? Do you want to do something tomorrow night at seven o’clock?”

He’s expecting attention. She doesn’t give him attention. What she’s saying (in her head) instead is: “That’s all good. And by the way, I’m not going to get into this with you. Because why would I, right? You have your reasons, I have my reality. What I’m more interested in is my reality, not your reasons. Your reasons may be true, your reasons may be accurate, you may not be lying, but I’m interested in my reality—in other words, in the result I’m getting, and the result is nothing’s really happening between us. And this is a poor text exchange. So my reality is what I’m responding to.”

Respond to your reality, not to his reasons.

“Have a great week.” Smiley, happy, positive, polite, but low investment.

I knew that this would scramble his brain. She’s kind of checked out a little bit, even though she’s still being polite and warm, which is what kills a person. When you’re still warm and polite but you’re moving on and doing your thing, that affects them deeply.

Here’s what he sent back: “So does that offer still stand for hanging out? Or is that a one-time deal? I’m free if you’re available. Would be nice to talk at normal speed.”

So this is a guy who suddenly got vulnerable. He realized that he wasn’t getting anywhere, that she was checking out, and that he needed to actually start to invest. So he puts it all on the line.

Here’s what I told her to write back: “It’s dangerously close to a one-time deal . . . ;-)”

Now, by saying that, you’re actually introducing that element of danger: “This might not work out for you now as a result of what you’ve done.” But there’s a little playful emoji there, a little softener. “What did you have in mind?”

So here’s where you’re not doing the work for him. Instead of her now saying what she said in the beginning, which is: “How about date tomorrow night at 7?” instead, she’s putting him on the back foot: “You’re coming after me, so what did you have in mind?”

To which he replies: “Why don’t we meet at Harlowe for a drink tomorrow at 7?”

She then says: “Okay, see you tomorrow.”

This is a tempered response, but it’s warm. And it does exactly what we always intend to do: To show the person opposite us that “I will invest if you invest, but I’m not going to invest simply because I like you. This is an equal arrangement: you give, I give.”

You may have noticed that dating today is fraught with situations where nothing seems to happen. You’re either on dating apps constantly burning out because messages never turn into dates, or you’re dating people where dates and hooking up never lead to a relationship. There is a fundamental problem these days with lack of momentum in dating.

Now, some of that is the fault of the people we’re dating because there’s no proactiveness about them. There’s no intentionality in the way we date. And in fact, that’s a big part of the problem. But the bigger part of the problem is that we tolerate it too often and we don’t know how to get around it. We don’t know how to say “no” quickly to the people who aren’t giving us any momentum. And we don’t know how to take someone who could be more proactive, and encourage them to do so by the way that we relate to them and the standards we have.

So much of this can be learned. And it’s a language that changes your dating life once you have it, because all of a sudden, you’re someone who actually gets progression in their dates, not someone who constantly gets stuck in the casual phase.

Creating Momentum

I have a program called “The Momentum Texts” that shows you exactly how to do this with 67 specific messages of momentum that get things moving in dating. You’re really going to enjoy this. It’s also the price of a Starbucks coffee these days, so it’s a very easy program to get your hands on. Go over to MomentumTexts.com and grab your copy right now.