How to Be Unforgettable on a Date

The truth is, we all want so badly to be unforgettable on a date . . . but actually making that happen can feel tricky.

In today’s video, I give you three practical ways you can enhance the impact you make on a date.

Be sure to stay until the end of the video for a special gift. It’s somewhat vulnerable, and it’s a little different, but I think it’s something that’ll stick with you . . .

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Hey guys, before we get into this video I wanted to let you know, this video is all going to be about how to make a massive impact on a date, how to make yourself unforgettable after a date. At the end of this video, I have something really special that I’m going to give to you, that has a massive impact on the way people come across when they meet someone that they want to attract, or make an impression with. Stay until the end of this video. Watch this video, because it’s an amazing introduction to everything I’m going to talk about. But then at the end of this video, I have a free gift for you that you are going to love. Let’s get into it.

How to be unforgettable on a first date. The advice I’m about to give can work for any date really, but on a first date we get particularly nervous, don’t we? We worry about how we’re going to come across. I want to say firstly, that despite what I’m about to tell you in terms of how you can enhance your impact on a date, it’s your date. It’s a date that’s 50% you. It’s your thumbprint and your thumbprint is yours. You can’t get it wrong. It’s yours, it’s you we are talking about. So while I’m going to give you some ideas, some tips, some techniques, some thoughts, I don’t want you to overthink going on a date because you’ve watched this video.

I sometimes think that’s one of the negative impacts of what I do, is that it can lead to an overthinking. I don’t want you to do that. I want you to think that even if you didn’t do anything by the book on a date, someone can still fall madly in love with you, and decide to want to be with you forever and marry you and have a family with you. This isn’t an exam. It’s you.

With that in mind, there are things that over the years of doing this, I’ve learned that, aren’t great enhancers for what we want to bring out on a date. For what leads to great conversation, for what leads to amazing connection, what leads to someone thinking about you after a date. So I want to give you today three specific techniques for enhancing the impact you can make on a date.

Number one, “Start on the Ground.” One of the things we do on a date, which could be characterized as the really difficult small talk section of the date, is we see someone and we say, “Hey, how are you?” It’s a really difficult thing to answer because where do you even start from that place? It’s not that it’s a bad question. It’s just a difficult question to answer. It’s hard to answer honestly, because our answer to that is always extremely complex, and it’s also hard to answer specifically because it’s such a big and vague question. It’s starting from 50,000 feet in the air.

I propose that you reverse that. You start on the ground and work your way up to the 50,000 foot view. On the ground would be talking about something that happened this morning or movie that we’ve both seen, that we really like, or something we’re excited about in the next month. Go on a date and ask yourself on the way to the date, what’s in the news of my life right now? What’s in the news of my week? What’s in the news of my last hour? What’s been going on? What unexpected thing happened to me just this morning?

By the way, I sometimes think that we get very caught up in life thinking that in order to have great stories, something fascinating needs to have happened to us, but that’s not actually true. The basis, of great story, is we need to have feelings about something that’s happened to us, however mundane. Whatever happened to you this morning, however non-eventful, if we have feelings about it, then we have story to tell, we have conversation. Talking about something that’s happened this week, or today, or this morning or how you feel about a movie you saw last night, you are immediately starting on the ground, which feels like an organic conversation, and then you can work your way up to the bigger questions about each other.

Number two, “Connect, Don’t Coach.” I always think that it’s really aggravating when we share something with someone that might be a little bit vulnerable, and instead of connecting with that vulnerability that we’ve just shared, and maybe even offering a little bit of their own vulnerability, someone takes the opportunity to start giving us advice. Which by the way, on a date especially, is a really unsexy move. Because you’re immediately creating a sort of mentor, mentee relationship. A coach, student relationship, a therapist, client relationship. None of these are sexy relationships in the context of a date and they also don’t allow for real connection. All they do is elevate one person above the other in a bit of an icky way.

If you said to someone on a date, “I really enjoy writing, but one of the things I’m working on right now is I get too in my head, and then I struggle to get down to it because I’m prejudging what I’ve written before I’ve even started.” If someone then takes that moment and says, “Oh, you got to do it every day. You can’t overthink it. You just have to set a time in the diary and every day, just go for it.” I feel myself getting aggravated as I’m hearing this interaction because it’s so annoying.

A beautiful thing you could have done in that moment is, if I said, “I prejudge too much what I’m about to write and sometimes I don’t get to it for that reason and I really want to work on that.” By the way, it’s kind of attractive when someone says I really want to work on that, because it shows a self-awareness but also a proactiveness. It’s not negative. There’s nothing negative about saying that and there’s nothing sort of poor me about saying that. It’s not saying, give me advice. It’s just saying I’m working on that, which is actually really attractive to meet someone who’s that kind of person.

That’s a great opportunity for someone else to say, “I so get what you mean. I so understand that because I always feel like that about creative stuff. It feels so good once you’ve done it, but it’s the getting into it that’s really difficult.” That’s just a moment of humanity. It’s a moment of connection. It’s also an invitation for someone who maybe doesn’t write or maybe doesn’t even have that issue in their creative world to talk about something they struggle with, “Yeah, I totally get that. It is really tricky, isn’t it? To get into something in the first place. I know that for me in my life, one of the things I’m working on is this.”

So what I’ve done is I’ve taken your vulnerability and said oh, I’ll reward that with my own vulnerability so that we can have a moment of connection. Thank you for being brave. Thank you for volunteering something about yourself that takes courage. I’m now going to reward that by doing the same from my side. We’ve come to the table and set down our weapons. But instead, in so many situations, someone lays down their weapons and the other person says advice. Instead of using the moment for humanity, someone uses it for superiority.

Lastly, number three, “Listen and Capture.” Without a doubt one of the best pieces of advice for any date or any meeting with someone, business too, because so much of this stuff works for job interviews. It works for client meetings. It works for pitch meetings. This is stuff that is to do with attraction and not just in the romantic sense, is being present. Being present with what someone is actually telling us, which starts with asking questions. In order to be present with what you’re telling me, I need to ask questions. I need to be curious about you in the first place.

Now, listening, active listening, really sort of tuning into what someone is saying, you ask a question and then you really listen, instead of thinking about what you’re going to say next, instead of thinking about how impressive your response is going to be. Instead of listening to someone who says that they went to a part of the world and going “Oh, I’ve also been to a part of the world,” which we do all the time. We call it story trumping, finding a way to take their story and one up them because you want to show that you’ve done that thing too, or you’ve done something cool too. I’m impressive too. That’s a problem. But really connecting is asking a question and then just listening to what they’re saying. Being impressed by something they’re saying, being even more curious about what they’re saying. Or if you don’t understand what they’re saying, asking another question.

But listening isn’t the only part of this. The reason this particular part of this piece of content, this video is listen and capture is because the capture part is really important. I remember being in an interview or not an interview, a meeting, an initial kind of pitch meeting, I suppose, with a company called Influex. There’s this wonderful gentleman over there called Dima. Dima and his team were pitching to design my new website, Go check it out. It looks shiny and brand new because of everything that Influex has done and it’s beautiful.

In the first meeting I had with them, one of the things that stuck out to me was that Dima got me to talk a lot. He got me to talk about my vision. He got me to talk about what I’m excited about. He got me to talk about where I wanted my personal brand to go and what I wanted to do. He really looked to understand my current frustrations, my goals, what I’m trying to do, where I’m trying to transition to, all of it. He really listened, along with his team, wonderful team. Kind of three quarters of the way through the call, Dima repeated back to me what I had said in sort of his own words, but also mine, in a way that captured the essence of what I was getting at.

He said, “So let me make sure I understand. What you really want to do is,” and then he said this and this and this and this, and you’re frustrated because right now, blah, blah, blah. What you’re really excited about is this and this is where you want things to go.” I sat back and I went oh, he gets it. He gets it and it was that feeling that he got it, that made me decide to go with them and not a different company because I went, “This person gets me. They understand the essence of where I am right now.”

The reason we’ve used this language capture, Jameson made this wonderful point about photographers. That when we think of a great photographer, we think of someone who’s captured the essence of a moment. Of a street corner, of someone outside busking in New Orleans, of a moment between a mother and child. We feel like we compliment them on their eye. Don’t we? Because for a photographer, there’s a listening period, of course, literally a watching period. There’s a period of just what’s going on here? What am I trying to capture? And then there’s the moment of capture and when we look at a great photographer’s photo, what we say is, wow, what a great eye. That photographer has been able to see something and capture it in a way that other people couldn’t. It’s their ability to capture the essence of the moment that makes them great.

Well in conversation, it’s our ability to capture the essence of somebody else or of what they have expressed to us, that makes us truly stand out and be unforgettable to that person because they feel understood by us. They feel we have perceived something about them that is not commonly perceived, or that demonstrates an awareness of who they are in a short space of time because we really listened. That builds intimacy and intimacy makes you really hard to forget. It makes you very hard to not call after the date because someone feels that you’ve really captured them.

Now, if you are thinking to yourself, but I . . . If you get to a part of the date and you’re like, “I want to recapitulate what they’ve said to me in a way that shows I understand them, but I don’t feel I understand them,” well that’s a good litmus test. Because at that point you can ask more questions. Well, what is it I don’t understand? What is it I don’t know? What is it that’s making it hard for me to sort of capture what they’ve said to me? Well, I don’t really know what they quite meant by that. Well, I don’t really know how they feel about that. Great. You now know the next most pertinent questions to ask someone on a date that are going to build that connection.

Let me know what you thought of this video in the comments. I have something that I’m really, really excited to give you right now because it’s very raw. It’s very vulnerable from my side, but it’s something I know is really going to help you, if there is someone you want to make an impression on in your life. What I’m about to give you was born out of a radio appearance that I did.

Now this show that I did got an amazing response from people. We had thousands of tweets coming in and messages and the show got amazing feedback. My brother Stephen called me afterwards and he said, “That was incredible.” He said, “You’ve made such an impression, but I know that there were specific things you did to prepare for that, that people don’t know about. People often think that you are sort of spontaneously impactful, but they don’t realize that there are certain things that you’ve learned that they can learn too, about how to have a massive impact in the first five minutes.” He said, “Do you mind if I create a guide that expresses these? That actually shows people what they are, so that they can learn them?”

I okayed it and he went away and created this guide. It is called the First Five Minutes and what’s so cool about this guide is that, it plays you the interview that I did, and then it has Stephen breaking down the things that I did in that interview that you can learn too, whether you want to apply it to making a huge impression on the first five minutes of a date, a job interview, a sales meeting, a pitch meeting, a client meeting. Wherever you know, I want to maximize my impact on someone when I meet with them, this is going to be a really valuable set of techniques. So go check it out. It’s at That’s the word first, the number and it’s a little vulnerable because it’s Stephen psychoanalyzing me and my behavior, but it’s also really helpful. I still, to this day, get DMs about that show and Stephen’s guide that broke it down from people who said, “I learned so much from Stephen’s breakdown.” So I look forward to hearing your feedback on this. It’s at I’ll see you over there.

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5 Replies to “How to Be Unforgettable on a Date”

  • Thank you so much for your knowledge and sharing. I wonder what to do when one’s date doesn’t stop to draw breath? How does one actually get to say something in the conversation without interjecting and being rude? Thanks again.

  • story trumping lol!.. ive never heard it put like that.. i hate that.. its like “um, ok.. are we trying to get to know each other or is this a contest and a competition i didnt know i was in… :? ” lol…… its one thing just also sharing a similar experience and the joy in it, which i do from time to time.. and then there’s that.. i really like the really being present to hear what someone is really saying.. and even if someone isnt being honest and transparent.. if we are present enough with that active listening we can sift through the lines of what they only want to present to us.. which i have to end up doing more than often to be honest.. its only seldom someone speaks to meand i dont have to do that work.. every now and again when it happens , of course it take me by surprise.. for one.. then next that they could somehow communicate to me on eye level :/ :).. and when it happens.. its really like im blindsided, but in a sweet -thoughtful intricate kind of way…. if that makes any sense.

    i did check out that interview at **.. and it was really candid lol.. thats the more unfiltered you i imagine lol.. altho i didnt get time yet to read the pick apart you mentioned your brother did of you.. i will when i have some time to read it.. but i loved that interview as well.. seems thats the you.. the masses wouldnt really be able to handle lol

  • I honestly can say that this video came at such a great time: I’m having my first date soon and I’m VERY nervous. Not that he’s not a great guy, I’m just awkward as hell

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