Man Humbles Room Full of Women . . . And It Was Me??

Who pays on a first date?

Six years ago, I made a controversial video tackling this very subject, and it went viral.

So this week, I decided to make a reaction video to my own video. Do you remember watching this video the first time around? What are your thoughts? Tell me in the comments.

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Man humbles room full of women.

So we made this video years ago, back in 2016. We were on tour at the time. I remember this event, Jameson, we were in LA. We were almost about to wrap up. It was literally the last question. I said, “any more questions, let’s do one more.” It led to us chopping a moment from this event and titling it for YouTube, “who should pay on a date?”

Well, the video went viral to the tune of tens of millions of views. Which I don’t know if I ever told you this, Jameson, but I ordered a pizza once. And the pizza guy saw me when he arrived at my house and went, “You are the who should pay on a date guy.” That’s how viral it went.

Here’s the crazy part. This video has really had legs because this year it went viral again. Now it didn’t just go viral, it went viral via several content creators who all titled it the same, “man humbles room full of women.”

Humbles, Jameson, I mean, they weren’t just a room full of women. They were actually our fans. They were people that liked us. So it was a tour of it. It was my tour. I didn’t just walk into a coffee shop and humble a room full of women. I’m always concerned about divisive language like this. Because our biggest ethos is about bringing people together, not dividing them. I want to bring men and women together. But we’ll see, I’m gonna see how much of this video I still agree with. Don’t forget at the end of the video to go to, where based on your specific love life challenge that you enter, I give you the best one of my solutions to help you right now. OK

Speaker 2:

During the dating period, you know, after like four or five months of dating, I just wondering at what point does it get, do you have to pay, do the woman have to pay when they go out? The guy is asking that I should, there should be half and half at that point when you already-


At what point?

Speaker 2:

When you already been dating for four or five months.




I can immediately remember how I felt when that was asked, because there was something about the idea that after four or five months he had the gall to want to go halvesies that immediately irked me at the time.

Look, okay, to give you a quick answer on, firstly, I think we should just deal with the who should pay thing to begin with. When you’re on a date who should pay?

This is why I think this ended up becoming the video that it did. Because of the unanimous, I don’t think every woman in the room did say man to be honest, I think it was just-


Just enough.


There was enough. It was audible, it sounded like everyone in the room said it, but everyone in the room didn’t say it.

Speaker 2:

I know. I mean, that’s what I told him. You know, I’m sorry, I say, I’m dating, we’re dating, you’re the gentleman here, you should pay.


Yeah. Okay.


So she . . . I hadn’t remembered exactly what she said here, but she says, you know, basically “I tried to tell him, we are dating, you are the gentleman here, you are supposed to pay.”

And it’s that word that I think helped the viral quality of this video. Because I think that a lot of men hear that “you are supposed to,” and that’s what immediately gets their backs up.


He’s supposed to pay.

Speaker 2:

Yeah. That’s what I told him.


But you are supposed to have sex with him whenever he says?

Speaker 2:



I really went for that one, didn’t I? Look all the jewelry I’m wearing. Who did I think I was, Johnny Depp? I look like like an aggressive Jack Sparrow having a go at a room full of women for stealing his treasure.

Speaker 2:

Whenever  . . .


But where does this double standard come from? I’m sorry, it’s the reality. You guys can moan at it all you want. But the moment you say to a guy, “You have to fucking pay for my time.” You’re saying this relationship isn’t equal.

I don’t think I would deliver it with such anger anymore. This relationship isn’t equal, my time is worth more than yours, so you should pay for it. I wonder what paradigm that sets up.

The point that I was really making there is that entitlement on either side can become a really ugly thing. Whether it’s entitlement from someone who thinks the other person should always pay. Or whether it’s the entitlement of a man when it comes to sex and you owe me this because we’re at this stage in the process. None of us like to feel someone else’s entitlement. So we have to be very wary of that entitlement in ourselves.

Here’s my view. If you go on a date with a guy and you don’t offer to pay your share, you weren’t taught right. If you go on a date and he doesn’t pay, he wasn’t taught right.

I l broadly agree with this still. The idea that on a date, it is the polite thing to do to at least offer to pay your share. I also, by the way, think that you learn more by doing that. You learn that they didn’t do it because they had to, they did it because they wanted to. You also give them the satisfaction of being able to say, “no, no, I’ve got this.” That’s the most satisfying part is telling someone, “no, I’ve got this.” It’s not satisfying if someone says, “you’ve got this.”


I can tell you right now. If I was dating someone and they never offered to pay, I wouldn’t be dating them. I can tell you that now. If they never offered to pay, I would not be dating them because I’d say this is the most polite they’re ever going to be. And they’re not even trying to pay now. What does that say about my future?

The future point is an interesting one because Alain de Botton, I remember him once saying that when you have an argument with a partner about something they did that you didn’t like, it upsets us so much, not simply because they’ve upset us in the moment, but because we project into the future all of the ways that this behavior is going to affect us and continue to make us unhappy. So you’ve made me upset right now becomes you’ve ruined my life.

Similarly, in this context, he’s not just seeing a situation where you are not contributing right now, he’s looking at an entire future where he is the sole person paying the bills.

Let me come at this from a different angle. I would be treating . . . I will always treat my partner how I would treat my best friend. And I wouldn’t apply a different standard to my partner than my best friend. I wouldn’t go, I wouldn’t say to my best friend, “Let’s always go out to dinner and you always pay.”

That’s a good point.

I’d say, “Let’s be teammates here in whatever way we can.” And maybe by the way, proportionately what you can do is less than what he can do. That’s a different thing. If he says to you, “I want to go stay at the top hotel in Big Sur this weekend.” And it’s 1500 bucks a night and you say, “I don’t have the money.” It’s his job to say, “it doesn’t matter, I didn’t do it so you could pay. I did it because I want to go and I want to take you.”

That’s a good point. I think that point relates both to well into dating, but also a first date. If you are the one to invite someone on a first date then, it feels organic and natural that you would be the one to pay. Similarly, four or five months in, if you want to do a trip with someone that happens to be expensive and you are the one who says, “I want to do this trip with you,” or “I want to take you on this trip,” or you say, “I want to take you to this really fancy restaurant.” Then it stands to reason that you should have already calculated that you are willing to pay for that because you are the one who’s put forward the really expensive suggestion. That’s especially true if the two of you are in very different financial positions.

Great. That’s what that is, right? Or if you both agree to go on holiday and you have a fifth of his earning potential, you say, “I want to contribute to a fifth of this holiday.” It’s overly simplistic, but you get what I’m saying, right? I will contribute on the level I can contribute. Let me tell you what means something to a guy, trying. That means something to a guy. When he feels that you’re not even trying to contribute, that’s when he feels used. Because any guy who’s really confident and self-respecting, if the woman never is even trying to contribute, he feels like he’s being taken advantage of. And it has nothing to do with money. It has to do with the lack of gesture. So I would be looking at, if you like this guy, maybe if you’re in different positions, figure out what you want to contribute proportionately or what you can contribute proportionately, and treat him as you would your best friend.

It’s really sweet that idea of treating someone like your best friend. I really stand by that. Because that’s, I mean, what is our partner? But the person that has devoted their lives to us. Who has said that you are the one person that I’m going to be with romantically. Doesn’t that person deserve the best of our generosity? Don’t they deserve the best of our teamwork, of our support? Why is it, and this is I think a problem with so many relationships, is often the person that does the most for us gets the least from us. And we take them for granted.

I think about this video as a whole. And that idea of teamwork to me is the idea that stands out the most. Because we can have all sorts of rules around this, but rules can only get us so far. And rules really, when you have a rule, it’s only ever really getting at a principle. And the principle is the thing. The rules can be too rigid. Like, we shouldn’t have a rule that says every time someone pays for something, you contribute the amount that you can in proportion to how much you earn compared to them. No one wants to do that.

It might be that that person pays three times in a row. But then on the fourth time, you’re like, “I got this.” I mean, in any relationship, that’s what means something to everybody. Not just men. Is that feeling that somebody else is trying. And trying can come in different forms. Trying can come in the form of, you do something for someone and they show a lot of appreciation for what you just did. Trying can come in the form of, I’m going to contribute what I can because I want to try. It’s all in the spirit of teamwork.

I always think it’s kind of nice if you are offering to do something expensive and someone else says, “}oh, that’s so much money, we could do something else.” Even if you know you’re going to do that with that person anyway, because you want to spend that money. Just the fact that they were watching your wallet for you is a beautiful thing. That shows me I’m with a teammate. And when we feel like we have a teammate, we start to trust somebody. And trust is the beginning of a real relationship.

I also want to say this. We live in a world today where dividing the genders gets more clicks than bringing them together. Jameson, you mentioned something before this video where you said I think on the Ezra Klein podcast, you heard that the difference between TV and social media is that on TV, you are rewarded for likability. And on social media, you’re rewarded for attention. Which if you think about it explains why man humbles room full of women gets more clicks than . . .


Guy makes a nice point about teamwork in a relationship.


Don’t get mugged off by the rhetoric out there that is designed to make you angry at other people. That is designed to make you angry about the opposite sex. It’s all designed just to get your attention. It’s not designed to help you have better relationships.

And ask yourself, by the way, if any of these videos that you watch are making you angry? Has getting angry ever led to a better quality of relationship in my life?

Before you go anywhere, go over to, where I have a tool that you can literally tell your dating issue, and it will recommend you the best solution to what you are going through from my archives. Check it out. It’s really cool.

And thank you for watching all of these years as I’ve been cursing and getting somewhat aggressive at times spontaneously. And all these years you’ve just been here. So I suppose tis I that has been humbled, Jameson, by all of your love. I’ll see you soon.

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3 Replies to “Man Humbles Room Full of Women . . . And It Was Me??”

  • Hi Matthew and team, I want to say thank you for all your videos to us women out here trying to understand the crazy dating world of today! Matthew you did have it right in Who Pays on 1st Date: it is about the law of reciprocity… speaks volumes about a persons attitude as a team player or taker… THATS the value system person is displaying with entitlement or not. Just my HUMBLE opinion.. LOL Colleen Ryder

  • Loved the info and perspective since I always believed it was basic consideration to offer to pay or contribute. I want a partnership, not a free meal ticket. Thank you for sharing this view and the underlying reasoning. BTW, your love bomb video- best ever, highly helpful!

  • I am a woman but have always offered with anyone to pay for my meal if going out.
    I don’t believe it should be left to the man even when on a first date.
    I think it’s always nice to offer. I think whoever invites the other person to a specific restaurant maybe the other person should pay or halvies.
    I have been dating my partner now for nearly 3 yrs & i either offer or we take it in turns, I buy this time he does next time. Especially if you both work fulltime. This won’t change even when we move in together next year. I like the comment made in the video of teamwork. You are a team going forward. It’s also manners. Years ago women didn’t work & sometimes married to work from home so did not receive a wage. Times are different, most women work. Some women amaze me to be honest.

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