Is a Great First Date a Red Flag?


A bad date—where we know we won’t see the person again—can be frustrating since it wastes our time. But what’s even MORE frustrating? An amazing date with someone who just disappears after seeing us only once or twice.

It leaves us wondering: “What the hell happened?? I thought we had real chemistry!”

In today’s video, I explain exactly why someone pulls away after a first date—and how you can tell the difference between someone who’s a keeper vs. someone who’s just telling you what you want to hear.

I just received the first box of my new book, Love Life. These are literally the first copies ever in existence of this book. This thing right here is four years of life for me, and it’s just a huge moment. I’m so so so excited. I can’t wait for you guys to get your hands on this. 

And by the way, when you do get a copy of the new book, we are also doing a really exciting giveaway that I’m going to tell you about at the end of the video. You are going to want to be a part of this. The prizes are ridiculous. You’ll see, but for now, on to the video. 

Why are great dates dangerous? Let me tell you. There was a question I received on a live session I did recently from a woman called Deborah, and here’s what she asked me:

“What to do if a guy you went on a date with suddenly disappeared, but the connection was just epic. He even gave me his favorite book. I have the copy. At least take it back!”

This is addressed not just to Deborah, but to anyone who is thinking about a great date they went on where someone had no follow-through afterward, and they’re driving themselves mad with the potential of what could have been. 

I think of these things as the unhatched eggs of our love life—the little eggs of love potential that we nestle and keep warm and think about and drive ourselves crazy with overthinking. 

Imagine the potential, imagine what that could have been. Now, Deborah describes an epic connection that she felt on this date. And this is where first dates can get really dangerous, because firstly, a connection is not character. Connections aren’t the only thing that make great relationships. Character makes great relationships: What’s their moral compass? What are their values? How do they show up in difficult situations? 

None of these things you can see on a date. They can only be shown over time, so someone’s connection with you is not an indication of their character, but it’s even more fundamental than that. The connection you felt with someone on a date isn’t even necessarily a sign of how great your connection is with the person. 

Now that’s a weird thing to hear. How can that be true? If I felt an amazing connection with someone, surely I have an amazing connection with them. But the problem is, a date is a measure of someone’s impact more than anything else. 

You can feel a great connection with someone who in actual fact is just really really good at creating the right impact. They know what questions to ask. They look in your eyes and listen intently as you give your answers. They know how to connect with your answers and be relatable and say, “Oh my God, that’s just like me. I find that too.”

There’s just this rapport that they’re incredible at creating, and this is, of course . . . I’m talking about those slightly more . . . not necessarily on the manipulative end of the spectrum although it could be . . . but just people who are really good with people. These are people who want to impress you, and what’s one way I know how to impress? Make an amazing connection with you. 

So some people are just really good at that, and in their presence, we feel so special, we feel so heard, we feel so seen, but if it was just on one date, then that wasn’t so much a measure of your connection with that person as it was a measure of their impact on you in the time you had. 

Then of course there’s the more innocent end of the spectrum. There are people who are just huge people pleasers who are also really good at making you feel heard and seen and connected, because they’re going out of their way to validate everything you’re saying. They don’t disagree with you. They connect with everything. They go along with everything and you think, “Wow, this person and I just have so much in common,” but really, what it is is someone who’s just eager to please you with the things they say. 

Have you ever met someone where you thought you had an amazing connection with them, but the more that time went on, the more you thought to yourself, “Oh, you were actually just saying what you thought I wanted to hear. This wasn’t really you.”

It’s also true that if we go back to that person who is just really good with people, or even narcissistic at the more insidious end of the spectrum, that these people can make us feel incredible for a short time, and then they get distracted and their attention goes somewhere else. And when their attention is on us, it is like a laser beam that feels so good, but then they move on. 

I’ve had that with people before where I’ve been so charmed by them. I thought we’ve had the most amazing connection, and then I realized they’re just charming. And it sobers me up, because I realize, “Oh, we weren’t going to be best friends forever. They just were really really good at connecting with me in that moment.”

So we have to stop telling ourselves the story about someone who was an amazing first date being someone who has huge potential for our love lives. One of the things that I talk about in this new book, let’s see what chapter it is—ah, chapter two: “How to Tell Love Stories.” 

For those of you who have pre-ordered, circle that chapter now—it’s about the false love stories we tell ourselves about situations that don’t actually represent any real potential. 

Of course, by definition, someone who just disappears after a date shows no potential whatsoever, but because of the connection we felt, we now tell ourselves an incredible love story about what that situation should materialize into. 

Remember, for a true love story to occur, you need not just connection . . . you need intention. You need investment. You need someone who’s actually committed to making the story go somewhere. Connection is not intention. 

By the way, when we want to craft a love story, we look for evidence that the love story is there. In this case, Deborah, you’re talking about the idea that he gave you his favorite book, but we have to sober up on that a little bit too, and be a little bit ruthless about it and say, “Okay, he gave me a book.” Maybe it was his favorite book, but it’s not a book he can’t obtain again. It wasn’t his first edition of his favorite book that he gave you. It was a copy of a book that he likes. He didn’t give you his grandmother’s necklace. He gave you a book. But that feels significant in the context of an epic connection. 

And by the way, Deborah, maybe you really did have an epic connection. Maybe there was something that wasn’t false at all. It was a real connection that you felt with someone.

But a relationship is so much more than a connection. Like I said, without a “yes,” without someone actually committing to us, a connection means nothing in the context of a life. 

By the way, this is an interesting thing to think about: When someone has no intention of a relationship or committing on any real level, when they’re not being intentional about their dating life at all, it’s really easy for them to come and make a big impact on you. 

I don’t know about you, but when I don’t have a care in the world, when I’ve got no skin in the game, when I don’t care how something’s gonna go, I am so relaxed. I am so playful. I’m so free.

And that can be seen as this incredible boldness and confidence and fun and sexiness. It can make someone have a huge impact on us because we’re just like, “This person’s amazing!”

How amazing they’re coming across can be a reflection of how little they care about the end result—that they have no skin in the game because ultimately, they want nothing long-term. The stakes aren’t high for them. And because the stakes aren’t high, they’re able to just show up in this really carefree, fun, confident way. 

Those of us who are actually trying in our dating lives, those of us who are actually being intentional about finding love—it can be a little more awkward as we fumble our way through it and try to find this thing that is really, really important to us. 

So to your original point, Deborah: “What do I do if a guy I went on a date with and had an epic connection with suddenly disappears?”

You give yourself the closure that you are looking for. You accept that his disappearance is already a form of closure—that it would be a terrible use of your precious time to continue to invest in this love story in your mind that doesn’t deserve your attention. 

You notice any moment where you feel your mind looking for ways to keep the story going, because that is such a human tendency. You’re not alone if you do that. We all do that. But I want you to notice even your language: “You know, I have a copy of this book he gave me. At least take it back!”

Even that is almost a desire to keep the thing alive. Like, “I’m waiting. I have the book. Come take it back!”

We shouldn’t even be thinking like that. We should get rid of the book. Throw it in the garbage. It’s irrelevant to you. You don’t need it anymore and you certainly don’t owe it to a person after a date to wait for them to contact you so they can take their book back. That is just another way we’re trying to keep the loop open-ended; a way we’re trying to keep the story alive for another day.

We can decide that anyone who has simply made an impact on me but has no follow-through is not a love story worth having in life. So I’m going to take my energy and direct it elsewhere.

If you want to create a real love story, that is what I wrote my new book about. It is called Love Life: How to Raise Your Standards, Find Your Person, and Live Happily (No Matter What).

And I have the final version of it—the copies that are going to go out to you—and I wanted to tell you about something we’re doing. We’re doing this incredible Love Life giveaway for everyone who gets a copy of the book from now until we launch, and that giveaway involves a 1-on-1 with me, and some people are going to win tickets to my Live Retreat in Florida, which is going to be unbelievable. We’re going to have Love Life sweatshirts to give away. Remember these? I’ve been wearing them in a whole bunch of videos. Well, so many of you said, “Where can I get that sweater?”

This was never even part of the plan. But we literally said, “Well, if we’re going to do a giveaway, we might as well get a few of these sweaters made up for people as prizes in the giveaway.” So you can win one of these, and also, even if you’re not a winner of one of the prizes, we’re giving everyone a ticket to an event I’m doing on May 4 called Find Your Person. 

It’s virtual. Everyone can come. Everyone who buys a book is going to get a ticket to that event, and we have some other incredible bonuses that we’re giving away to every single person who gets a copy of the new book regardless of whether you win one of the prizes.

But the good news about the prizes is there’s actually quite a few of them, so there will be a lot of winners, so head on over to, grab your copy, and you’ll see all of the information there about the giveaway that we’re doing.

This is a celebration, friends, so come be part of it with us. Once again, is the link and thank you as always for watching this video. 

Leave me a comment if you’ve already got your book and let me know how excited you are and what part of it you’re most excited about. I will see you in the next video.

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6 Replies to “Is a Great First Date a Red Flag?”

  • I’ve already pre ordered my book from Amazon I’ve sent you the invoice will I be automatically entered into the prize draw

  • Very informative video. I appreciate the detailed explanation. You are very giving in your videos; instead of serving the endless bait, like most online advertisers who try to rope the customer in, you actually offer substantial free content. I ordered the book because of that integrity you display. And, it must mean you have a lot more information in the book.

  • What about 4 great dates (the first 3 initiated by me) over a period of a month, after which (each time) he doesn’t text, but whenever I suggest meeting he’s enthusiastic and shows up? I’ve now decided NOT to initiate again… What do I text back when/if he gets in touch??

  • Matthew, you’re a gem. You’re such a blessing for your true and healing messages. This really delivers the answers that many are seeking. A perfect way to obtain the closure that makes it all finally make sense. Thank you, Matthew.

    You’re one of very few who deliver sincerely and lovingly at the same time.
    I pray you and Audrey every joy and bliss of a loving relationship, just as you keep putting into the world.

  • Lol – “get rid of the book (the date left with you)” – such refreshing & LIBERATING advice!!!

    Too many of us wait around & get suckered in again if/when these ultra charming, confident, low investment guys pop back into our lives!! Great video & advice as always Matthew

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