Who should pay on a date? Money, dating & dealbreakers with Matthew Hussey

Welcome to this very special episode of the podcast. Now, normally I get the chance to talk to couples in committed relationships about money, but there are a lot of aspects that I haven't been able to tap into. And I've been reading your questions and your comments and I want to talk about money and dating. Like how do you handle money if you just met? Or what if you've been dating for three months and and your partner invites you to Tahiti but you can't afford it? How do you navigate that situation? What do you say? And how do you handle the emotions that naturally come up when you're first starting to talk about money? Well, what I wanted to do today is to bring on my friend Matthew Hussey. I happen to think he's one of the best minds on relationships out there. And on a professional level, my team, we really admire the work that he does. There are a very, very small number of people who we admire in the self development world and Matt is on that list personally. He and I are good friends. He came to my 40th birthday party. So to just get to sit down and talk to him for hours was a blast. And I think you'll gonna hear that in today's episode. By the way, he and I recorded two episodes. One is this episode that you're listening to right now or watching on YouTube. And another is an episode that I recorded for his podcast, Love Life with Matthew Hussey, where we covered all kinds of other material. So I would encourage you to check out his podcast. Check him out on Instagram hematthewhussey and you can find his programs@howtogettheguy.com now, on today's episode, we talk about money in dating and relationships. We also cover things like why is it so hard for men to connect with their feelings? What are some of the common money questions that Matt hears from his clients who are primarily women? And I'll also share some things that I've never shared, like what would be an instant relationship deal breaker for me. Now, I joked with Matt that it's just two bros talking about gender issues, but I want to acknowledge that this can be sensitive material. And he and I always try to be as respectful and thoughtful about different perspectives as we can be. And I hope you hear that in our conversation today. So feel free to listen or to watch this on YouTube. I can tell you that I had a blast talking to Matt. So here we go. Okay, Matt, there's this famous video of you that's gone viral like 10,000 times. And every time I see it going viral, I go, God damn, this guy. How did he get this video to spread so much? You know the one I'm talking about? Right.

Who should pay on a date?

Yes. I want to walk through what happened on that video. I want to know the behind the scenes. So there you are on stage. How many people were in that audience?

There must have been about, I want to say, 2 or 300.

Okay. And is it primarily women?

Mostly, yeah.

Okay.

Almost all.

So you're on stage, you're doing your thing, and you have a Q and A portion. And this question gets asked. Do you remember how she asked the question?

Yeah.

She said, 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? Did 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 when you already been.

Dating for four or five months.

Right. How do I get him to go back to paying for everything? Was essentially the question.

Okay. When you heard it before you started to answer, there's always that moment where you're like, how am I going to answer this? What went through your head?

Well, the thing is, I thought she was gonna go in a different direction with the question itself. I almost thought she was gonna say, you know, he's been paying for everything for a while now, but I wanna start contributing because it would make me more comfortable. And it just went completely the opposite way. It went a shocking way to me because I didn't know how to. It really was, like, a slightly haunting question because it was like, are you really asking me that? Especially in front of an audience? There was no shame about that. It was just, how do I get him to keep paying for everything?

Yes. So then I waited to see the audience's reaction. Do you remember what it was?

I remember the audience was quiet and I sort of laughed before I even answered because I remember thinking I'd need to bite my tongue a little bit here, because I could tell immediately. Oh, I'm like, the question itself. I was so incredulous that that was the question that I. There was some part of me that was like, this is insane. Why would there be this expectation? And then that was probably why it was funny, because I recently did Red Table Talk with Jada Pinkett Smith, and they said for the promos, they wanted to use the video from who Pays on a Date, which is hilarious. We're bringing it up because it's like, fucking video haunts. Keep going back to that video. And I watched the video again because they were like, we need you to sign a release to let us use this video in the promo. And I watched it again, and I saw, cringed, and laughed at myself because I was like, why am I so angry? It was like, I would never answer a question in that much of an angry fashion these days. But I think that there was a part of me that was, like, almost affronted personally, that, you know, why is it our job to just. Why is there this expectation that is one thing to say on a first date, I expect the guy to pay. Right. I have my own, you know, theories on that. But. But that's, to me, a whole different thing than three months in. Yeah, he's been paying for everything. And your question to me is not, how do we even it up a little bit? The question is, he's now asked me to start contributing, and this seems wildly inappropriate. So I kind of. I let the audience have it a little bit on that one.

I love that you did it. So I remember watching this, you know, I told you I've watched it, like, hundreds of times because it was a masterful answer to a question that, as you said, was surprising. But also, the audience was not really on your side. Not at the end, not. They were not on your side. And I thought you handled it really well. You told the truth. It would have been really easy to say something that would have been crowd pleasing, but I thought you were very honest about it. And I think that in Money and Love Topics, there's a lot of material that is beneath the surface. It's not written anywhere, but is nonetheless real. And it's very easy to all sing Kumbaya and say, like, why don't we just, like, figure out a way that works for us? Okay, fair enough. But when you talk to couples and you talk to people, you realize there's some real questions and ways that we need to navigate. It's not always easy. So I. I love the video. I've made fun of you for your dirty shirt in that video.

The stained shirt, which I have explained was, I didn't go to my tour event in front of an audience of hundreds in LA with a stained shirt.

Disgusting stained shirt.

I'm like, people hug me before the event, and I got many faces of makeup imprinted onto my white T shirt.

You tried to make us feel sorry. Hundreds of people hug me to show their affection, and that's why my shirt looks so ratty on this viral video. I was like, am I supposed to feel sorry right now?

If a video is going to go viral, you'd rather it be a video of you in nice, clean shirt.

It's like, going viral. Like. Well, my equivalent would be me having a unibrow. Right. It's like, I really don't need to be filmed on that day. You know, can we just, like, give me till Tuesday? That's the.

That's the unibrow day that you don't go to. Your. Your audience isn't capable of giving you a unibrow right before you go on stage.

Okay, you got me there. Damn, you are good. All right, well, this is why I. I get to ask you the questions today. Oh, my God. All right, so you speak to many, many of your clients. There are almost all women. And what I love is the topics are visceral. They're real. They're about dating, they're about attraction. And naturally, at some points, money comes up. So what I want to do is I want to get your perspective on how money plays a part in dating and attraction and relationships. You see some of the similar things I see, but you see them through a totally different lens, and your audience is different, and I love that. It's like we're so much complementarity here. So I have a few questions for you. Who knows where the conversation takes us? First off, what are the most common questions that you get from your clients as it relates to money and relationships?

Suppose there's those early questions of, you know, who should pay? There's the insecurity or fear going into a situation that whatever, you know, my emotional money baggage is, is going to create problems for me in dating. Anytime we go to a date, we're buying and selling at the same time. Right. So interesting.

Meaning what?

We are deciding whether we want a person, but we're also simultaneously trying to be someone they want.

Yes.

And so there's this simultaneous thing of I'm trying to, on some level, be impressive and attractive, and that's the leverage. I'm trying to create leverage. And at the same time, I'm trying to see if I actually want what they have to offer. The reason I say create leverage is because if. If you get, you know, after a date, there's no point discussing how right for you someone is or isn't if they're not asking you on a second date. Right. The leverage is, do they actually want to continue seeing you?

What about when people say to you, why do we need all this artifice? Why don't we just be ourselves?

Well, I. We should absolutely be ourselves, assuming we have a clear sense of what that means and who that person is. I mean, a lot of us are. Being yourself is an interesting concept because it's a bit of a moving target, isn't it? We're always in discovery mode with ourselves at the same time as looking in the rear view mirror and saying, who have I. Who have I been until now? I once asked my mom, how do you know who you are? And she said, well, I know who I am because of what I've done and what I'm comfortable with. I said, that's a pretty good definition, right? We look in the rearview mirror to see who we've been so far. And now what we associate with ourselves is really in huge part down to the way we've been living, what we've been doing, what we perceive to be within our comfort zone. And so it. It's not always a good predictor of who we will be in five years or who we will be in 10 years based on how we expand our comfort zone. And, you know, I do things today that I never knew I would enjoy until I did them.

Yeah.

In the same way that there are foods we like that we never knew they were our favorite food until we tried them. So who we are as an evolving thing, be yourself. If we're not careful, be yourself. Rather than being a mandate to step into your own skin confidently and be, you know, true to yourself, can end up being a kind of excuse for not developing or growing or doing whatever is the path of least resistance for you.

I agree. It's. If somebody asked me, who are you to me, I don't even know if today I would have a good answer. I might naturally resort to, I'm a husband, I'm a son, etc. I'm a teacher. I might say I like travel. So now I'm getting into my likes. But when we say be ourselves, it's not really clear what part of myself means. I might say I'm. I'm generous, but how does that show up on a date? And so, yeah, it's interesting, this be ourselves concept, which is simplistic.

Maybe it's hard. It's a sort of hard thing to latch onto. I mean, I suppose people like Eckhart Tolle and people who spend their lives talking about mindfulness and the self being an illusion. Anyway, it starts to get really kind of mean when you get to that level because you go, well, all of these things that I've decided I am are just constructs anyway. They're just an ego that I've created. I am, as they say, the observer. I'm not the thing that I think I am. That's not me. And identifying with self, people who are experts in that world will say is the problem.

So when your clients ask you questions about money, it starts off with, you know, who pays for the first day? It's a very visceral moment. What else? What are the most common ones?

It might be I, you know, I deal with a lot of women who make more money than the men they date. So it might be, how do I deal with a guy making less money than me? And the insecurity that can come with that or the emasculation that can come with that.

Very loaded, vivid words. That's what I really enjoy about this topic, because the word insecurity and empowerment and he doesn't feel masculine. That's real. That, that's very, very vivid. Okay, what are the most surprising questions you get? The questions where you go, wow, I would have never asked that one.

You know, I always struggled a bit with how much the, the people that come to me talk about being intimidating because I, and, and, and I want to preface this by saying that there are many, many, many, many women. It is, there is a genuine problem with strong women intimidating men. There is a real problem. Agreed. So I don't want to, I don't want to gloss over that. It's a real thing. And there are plenty of men out there who have no concept of how to deal with a woman who does not need them in what they perceive to be the traditional ways.

You know what my friends used to do, my friends from Stanford, they would tell me when they would go out to bars, people would ask them, oh, where do you go to college? Or where did you graduate from? And they stopped saying that they went to Stanford because the minute they said it, the guy would walk away. I was like, what?

So interesting.

Then when some of them became doctors, they were in medical school. When they would talk about being in medical school or being doctors, same exact thing happened. I don't think a lot of guys realize that. And I think probably every woman listening goes, duh, that has happened forever.

Yeah.

So it's really good to share that side of things that many guys don't realize is actually happening. Okay, so intimidation.

So that, that intimidation factor is a real thing. But I, I, I would always be trying to juggle that with what I saw as the other side of the argument, which Is that saying I intimidate everybody can be a bit of a copout.

Why?

There are plenty of successful people in life, and anyone who is in a position of power or success or has money has the potential to intimidate a lot of people or to make them feel uncomfortable. And yet we all know people who are in those positions who don't make other people feel that way.

What do they make them feel instead?

Interesting. Impressive. Equal.

Love it.

You always have to ask yourself, what are the weapons I've gotten really comfortable using?

Like what?

Well, for some people, it's looks. For other people, it's the amount of money they have.

Mine is my wit. On Twitter, when I crush these trolls who have no chance of intellectual parody, I go, why you bother? Just come to me after you studied for the next 25 years and you know how to try to troll on Twitter, you have no chance of winning this game. You think that that counts for me and Ramit?

That we always have this in joke that you. I want you to have a special account, like a Matthew Hussey endorsed account where you. I basically hire you to deal with our trolls.

No, no, you don't have to hire me. I'll do it for free. You don't understand. I love it.

You know, like, you know, like, was it. Where's the phrase from, like the Bourne movies? Say, send in the asset. Like, I like the idea that you're the asset and we just. I don't any. I don't need to worry about any of the ridiculous comments. I just send you in. Yeah, and you just handle it. And not even as me. You handle it as Ramit.

I go. Thank you for your email to Matthew Hussey. I'm Ramit Sethi and I'll be addressing your complaints from now on. We have three things we need to discuss right away. First of all, who made you think it was okay to send this email? That's how it begins already.

My favorite line is, we have three things we need to discuss. Discuss right away. It's already the greatest way to start that email.

It just comes so naturally.

Three things we need to discuss right away. That doesn't sound tweet length.

And then the next time you see me, you're like, oh, what's been going on? And I just pull out 300 pages of emails that I've been sending back and forth to people.

Yeah, yeah, yeah.

All right.

Everyone says, everyone, I'll teach you to be rich. Says, what's happened to CEO?

This is our. This is.

He's Handling some important matters over at Matthew Huss's company.

Okay. So I told you my idea for your business. Do you remember what I told you and Audrey to do to start a business? I said if I sounded like you two, I would literally start a competitor to Headspace.

Oh, yeah.

Where I would just talk and I would use my British accent and I would just say random words. I would say, you are beautiful. Can you say that into the mic, please?

You are beautiful.

All right. Throw that on a loop. I'm going to charge 4.99amonth for it. And I actually have. I did a little preparation for this because I would like for you to read a few things off the screen. Okay. Again, I think that you could come up with a very large business of just talking. And I put those headphones on and listen to the two of you.

Okay.

And go to sleep every night.

All right. We'll call it I will teach you to be British.

There's a little something I found on the Internet, which I was very excited for our conversation today. It's a meme. And the meme goes, british people having sex. Be like. And then they have a few words I would like for you to read off the screen. Just tell me if this is accurate. Just read them slowly into the mics.

I see how accurate this is. Oh, these are unbelievable.

Hear it, please.

So we've got. Oh, heavens.

Keep going.

I mean, that's like. There's. That's unbelievable. Scrumptious.

Keep going.

Yes, splendid. This is. This is a great one. I'm arriving. Three exclamation marks on that one. I'm arriving. This one's. I feel like this is more of an injury. You have to know British accents for this one. But this one is. It's Tuesday, innit? And Tuesday. Tuesday is spelt with chew C, H, E, W in it. I double N, I, T. It's Tuesday in it. That's. That's like a pro. That's like. In British. You can't even. You people. Americans don't know what in it means. And it means like, isn't it? Yes, it's Tuesday in it.

So out of all of those, what's. Is that? All of them to be missing?

I would say probably the one that's closest to me is. Is Tuesday in it? Because that's. That's more. Where I'm from in the UK is we're. We're all from the east of Lond.

Right.

My family. So we're all the Cockneys, the chimney sweeps on Mary Poppins represented us famously. And also I realized a lot of villains are. They have cockney accents.

Oh, yeah.

If they ever want to make someone seem grubby and conniving and sort of dark and evil, they give him a cockney accent.

So thank you for giving me the audio. And just to finish this whole, you know, thing off, we actually have the privilege of having your fiance here in the room. Audrey, can you confirm that Matt has indeed said in a British accent, I'm arriving?

In what context?

I think.

I think we all know the context.

That's too upper class for me. She knows she's much more posh than I am. She has absolutely. She is slumming it with me because she's from part of England where they talk with a much more. Yeah, they talk nice, talk proper, don't they?

By the way, every. Every American's like, what are you talking about? There's different British accents.

Yeah. No, Audrey. If you hear Audrey's accent, she's much more sort of upper middle class. I sound like the sort of. Well, the chimney sweep from Mary Poppins. So she's. Yeah. I thought. I remember when we first got together, I thought, like, this is posher than anyone I would have expected myself to be.

Do you think that the company of the two of you speaking, both affirmations as well as X rated comments, do you think it would be worth 50 million or $500 million?

Well, I leave that your business valuations, I. I leave firmly in your corner. But I have thought we should do some sort of like bedtime reading for people. Just like a bedtime story bedtime reading.

For like PG rated. And then perhaps bedtime for the more British X rated thing.

I assume that would be the sort of upsell there would be. Yeah, exactly. There'd be a freemium model. I'll take 10% in on Harry Potter level, sort of, you know, innocence, and we. We finish on some sort of dark, sordid cockney porn.

All right. Love it. Gosh, I feel like I accomplished everything I wanted to with this.

Yeah, we could interview.

This is. Wow.

I'm going to top that.

I'm stunned. You took it in a direction even I didn't anticipate. Thank you. Let's talk some scenarios. You're going on vacation with your partner, you've been dating for six months, and your partner says, I would really like to go to Tahiti. You can't comfortably afford it. How should you have that conversation?

You say, that sounds like the greatest thing ever, and oh my God, that would Be an absolute dream. I'm not in a position to be able to have a trip like that, you know, financially. I, I, you know, which makes me a little bit, you know, whatever. Insert authentic emotion there. I don't want to be the one letting the team down on something that you really want to do. And of course, something that would be awesome. But that's hot. That's really hard for me. What do you, what do you suggest? And they can say, what? Because what you need to know is you almost need to establish terms first. And the terms are, I can't come into this as a, as an equal partner. Like, financially, I can't come into that trip as an equal partner. And if that means that it's off the table, then that's important for you to know. Yeah, like, I could never afford my half. You can even be more specific. Like, I could never afford my half of that trip. And then you see what they say, because they may say, oh, that's a shame. Okay, well, no worries. Or they may say, I'm really mad because I really want to do that trip, but I want you to be able to do it too, but you can't. So, wow, that's annoying. And you say, well, you know, there's lots of things we can do that we can both contribute to and something I can do. I would hope that kind of a trip to Tahiti isn't the only way we can have fun. So then you're showing your versatility that you can do other things. Now they may say, well, it's okay. I don't need you to pay. I just want to do it as my treat. Now, you have two ways that you can respond to that. You can either say, thank you very much. Oh, my God, that's wonderful. I never would have expected you to do that. But if you feel comfortable with it, I don't want to get in the way of a really fun trip for the two of us. And if you genuinely are comfortable with that, then I'll do my best to enjoy it without worrying that I'm not able to contribute. My preferred option, which I think is the best one objectively, is to say, that's unbelievably kind and generous, and I feel really fortunate that you treat things that way. But I want to be able to contribute what I can. And it is not going to be a lot in the context of the trip, but it will be a significant amount to me.

I love that.

And therefore, I'd like to get X. You can even kind of compartmentalize what you're going to get. I want to get, you know, the.

The airfare, the Thursday night dinner.

Exactly. Whatever it may be, like, make it something that's. Instead of. It's just, you know, a monetary value which you can do. There's nothing wrong with that. But it's kind of nice sometimes to.

Be like, connect it to the.

Yeah, let me. Let me get the flight, or let me get this and. Or let me at least buy my own flight. I can't afford the hotel, but let me at least get my own flight.

And when you say that's your favorite, why is it your favorite?

Because it goes back to something that I know you believe in too, which is that. Look, I'll tell you a story. I was in New York once, and there was a night out in my mid-20s where everyone got a table that apparently no one could afford, apart from this one guy. And by the time the end of the night came and I was kind of a tag along on this evening, it wasn't my friendship group. So I felt a bit uncomfortable anyway because I was kind of like, well, I don't want to be that person at the table in the club who's, you know, just the freeloader. That makes me deeply uncomfortable. The bill came and everyone deserted. And this was like a $3,000 bill for a table in New York. And all the people that had been there enjoying it all the whole time, out of embarrassment, out of awkwardness, out of fear that they would somehow be roped into being in an in over their head, they kind of just deserted. And this person was left with this three grand bill. As it happens, the next night I was at dinner with that guy who paid the bill and a couple of other people. And I had left a little earlier, and I went the. The night before, and I went up to him and I had heard that he'd paid the whole bill. I went up to him and I said, Listen, here's $300. I wish I could do more, but I can't. But I wanted to at least do something.

Yeah.

And it was never something that he would have expected, but he turned around and he said, that is really, really nice. He said, my own friends didn't. Didn't even throw their card in. Yeah, you don't even know me and you've decided to do something like that is a really, like, I'm really touched.

Speaks to the character, your character.

And three grand. 300 off a three grand bill didn't make a lot of difference to him.

But the gesture really did.

But the fact that, yeah. His own. His actual friends didn't help.

Yeah.

And I was just the guy that felt like that was not appropriate for us. Just because we couldn't spend that much money, it wasn't appropriate for us to not do anything. And there is lots of situations in life where when someone has money, there is an. A natural awkwardness and an embarrassment a lot of the time among other people in the room and they don't know how to deal with it and how to handle it. And I chose long ago that my approach would be to. And by the way, when people are embarrassed or when they're awkward in a situation like that, even their gratitude tends to go out of the window. So kind of an interesting thing, because to come up to you and say like that night, to come up to that guy and say thank you so much is to acknowledge you haven't paid anything.

Yeah. Yes.

To just disappear is to sort of COVID your eyes and ears and just go, someone's got it. You really know that. Someone had to pick up that whole tab. But you're just like, oh, what happened? We were all on a night out. I don't know what happened. To say thank you is to acknowledge that someone has done something. So what I've noticed in a lot of situations like that is people don't even really say thank you because they're embarrassed.

Yeah.

I made a decision long ago that I would either genuinely and face to face acknowledge someone and say thank you and make sure they knew that I knew that they had done something, even if it was easy for them.

Yeah.

A friend of mine said to me once, a friend of mine who was much more successful than me, older gentleman, he once said to me, two things are always true when it comes to money, he said. And he was talking about when you have money. He said, everyone thinks you have more than you actually do.

Okay.

And everyone thinks you won't miss your money as much as they'll miss theirs.

That's interesting.

You know, I always made a decision that I wouldn't ever just disrespect the fact that it might be easier for someone because the person that can still go up and say thank you or say thank you, and here is what I can do. I know it's nothing, but it would mean a lot to me to be able to contribute something. That's the person you want to keep giving to.

Totally in your Tahiti answer. The thing that stood out to me, which you did so naturally. But I don't think it would come as naturally to many people. Was your first part of your answer was, gosh, thank you. That sounds amazing. I would absolutely love to be able to go on a trip like that. And then you got into the rest. That part, you just rolled over it because it came so naturally to you. But there's something very powerful about taking a second, slowing it down and expressing your gratitude. This partner of yours just invited you on a trip. That means they've been thinking about it, they've planned it, they want you to come along. The money part of it, of course, you need to address that, but the feeling that your partner wants you to be a part of this international trip, incredible. I find that when it comes to money, we are so nervous, this frenzied, harried energy that we immediately jump to things like, well, I could never afford that. And I just love how you slowed it down and you started from a place of gratitude. Very powerful.

Thank you. And. And you should never also be afraid to show someone that you don't need to do something like that. That, that would be amazing. But by the way, if you wanted to, you know, because I know that's a lot of money, we could always take a trip, you know, two hours away on a flight and go somewhere and still go and have an amazing vacation, but do something different. Like, I, trust me, you know, Tahiti, my God, that would be incredible. But, you know, I also, if it's too much, yeah, we could go here and do this now. They can still come back to you and say, oh, my God, no, I want to do this. I've been wanting to go there for ages. You're the person I want to go with. Let's do it. But just saying something like that is a beautiful.

I agree.

It shows someone else that you're a team player. You're watching. It's almost like you're watching their wallet for them. You're not even asking me to, but there's a part of me that, that I'm a team player and I, I want to support you. And when someone hears that, it's. It's a very powerful thing because you go, whoa, they're. They're looking out for.

They're with me, they're with. And life is going to present a million opportunities where there's going to be some price disparity or something, where one person says, oh, I want to do that, and the other goes, I don't think it's valuable enough, or I don't have enough money, et cetera, to be that versatile. And to remember that the point is not Tahiti. The point is for the two of you to create an adventure together that is powerful. I had to be reminded of that. I tried to plan a trip for my family. It was a very exotic trip. I think I told you about this, and it was a little too much. I learned. I was like, guys, it's so cool. I'll do all the travel planning. And then, you know, we talked about the travel and the budget and all kinds of stuff. And even though the money part of it I would have been more than happy to assist with, it was a little bit too much, too soon. And I was really down about it because I had planned and I had prepared. I presented a PowerPoint, and I just got blown out. You know, everyone was like, no. And I was telling a friend about it, and she said, well, you have a couple of options. You can be resentful or despondent, or you can remember that the point of your trip was to have a family reunion. And it could be there, but it could just as well be in other places. And sometimes I think when. When we talk about trips or even relationships, we have a vision in our mind of what we thought it would be. And when life throws us a curveball, it's really hard to grapple with that. Like, I was fixated on this place. In fact, this hotel, this lodge, this, that. And my friend, very savvy in her right, had to focus me on reconnecting with. What's the actual purpose of this? Is it the glitzy stuff? That would be nice, but it's really about finding some quality time.

That's exactly right. And you want to be someone who helps people connect to those truths. Like, be the person that helps someone else connect to those truths. When you're that person, they realize that they get better with you. They.

Yeah, it's inspiring.

It's inspiring. And you realize, you know, oh, this is what it's about.

Okay, when. When I was thinking about some of the questions that your readers sent you, and I listened to some of the questions that they ask on video, too, there's one that really stands out to me, and I want to get your take on it. This question about how do you have money conversations in early dating stages without coming across as rude or aggressive? And as a guy, I thought to myself, that's an interesting question, because I'm not particularly worried about coming off as rude. Well, I. I should be. I can. I can be aggressive, but it would never occur to me, oh, I need to not be intimidating or rude or aggressive. So I asked my wife, I said, what do you think is behind this question? She was, she just looked at me and rolled her eyes and. Okay, I can see it in your eyes too, that, you know, I didn't know. She goes, time might be an important component. Women often don't want to waste time if they are dating. Makes a lot of sense. Women might not want to scare him away. And I said, keep going. I was asking her like, what else? What else? And she said, you know, sometimes women aren't used to saying what they want and being rewarded for it. It. I said, what do you mean? She said, well, think about how we're raised and socialized. You know, be polite, don't speak too loudly, etc. So suddenly that question took on a whole new salience for me. The idea of how do I talk about money without being rude or intimidating or aggressive. Have you gotten that question? And what is your take on what that question really means?

Well, firstly, you could take out the money part. You could just leave that space blank and, and take that exact question and ask it a thousand different ways for women, which is, you know, how do I ask for a promotion without seeming rude and aggressive? How do I talk about the fact that I want a relationship without seeming over the top and aggressive? How do I like. There's so many things that if the women have as a fear of asking that men don't. Men are boldness. And even then, look at the language shift that I immediately shifted it to boldness when it was men.

Yeah.

Right. There's this natural kind of, well, if it's a guy doing it, then it's bold. It's, you know. Right.

I never assertive, I never worried about being bitchy, let's put it that way.

Ever. You, you just, you, you actually see it as a quality that you admire in yourself is your ability to be. No nonsense.

Yeah.

And ask for what you want. And it's, it's very often the moment it becomes a female question, it gets accused of being all sorts of other things.

Yeah.

Difficult, high maintenance, crazy, totally over the top, aggressive. Like there's all, all number of words that are designed to bring women back to a place of acquiescence. Yeah. And being passive and just going with the flow. And you know, men to a large extent, in dating, not every guy, but there's a lot of men who rely on that. They, they rely on that passive state because that passive state is actually how they get what they want. If I can convince you that you're being too aggressive or moving too quickly or asking for too much, then you might let me have my cake and eat it for longer. What I want to do is keep seeing you with minimal cost to me, and for it to be as easy as possible and for it to be on my terms. And the moment you start asking for things, you make my life less convenient. And I want it to be as convenient as possible. And the greatest trick I can play on you is making you think that what you're asking for is unreasonable. Because the last thing you want to do as a caring, nurturing, kind human being is be unreasonable. So if I can convince you it's unreasonable, then you're going to go back to a state of acquiescence. I will have won that battle securely. Because now you're. You're associating, talking about your needs, talking about your future. All things that men are. Men do all the time. They're happy to. They may not talk about their needs as much, but many men are really good at going out and getting their needs met when it comes to the future. Men plan well into the future about what they want. Right. You look at any guy with a business goal or with a, you know, fitness goal. Fitness goal. Men are quite capable of. Of looking into the future and. And delaying gratification and planning and making a vision for themselves. And then a woman comes along and says, hey, you know, what do you think about these things and building this together or how we would discuss finances together or whatever? And he's like, whoa, enough with the planning.

Right? Right.

This is a lot of future talk.

Yeah. So let's talk about how to have those conversations from your experience, whether it is about finances or I like our connection and I'm interested in a relationship. How would somebody say, how do I have this conversation without coming across as rude or aggressive? If one of your clients asks you that, how do you respond to that?

You always have to go into a situation, any negotiation, really, or any statement of what you want from the fundamental framework of this is about me. It's not about you. And I don't need you for it. All I'm really doing is seeing if you're the person I do it with. So now I don't. I'm not coming from an aggressive place with you. I'm just stating what I want for me. I'm talking about the kind of relationship I would be really excited to be in. I'm talking about the values that I think are really attractive when it comes to how people approach money. All I'm really doing is seeing what your reaction to those things is. And that doesn't have to always be done in direct ways. It can be done in very indirect ways. I saw an interview with Anthony Bourdain later in his life where he communicated that, you know, he's at a stage in his life now where he doesn't want to go and do 12 course tasting menus. He said, I'm, for me, where it's at right now is a great bowl of noodles.

Yeah.

You know, on the side of a street somewhere. If you feed me that, I'm happy. He doesn't need to tell you his relationship with money and food for you to know his relationship with money and food from that little story. And so what I think we all need to get better at is rather than asking someone a question that they don't know how to begin answering, like, what's your relationship with money? Is there a way that I can communicate through story? You know, I told you the fact, you know, the small thing about, like, When I was 26, 27, I bought a nice watch because I'd always wanted a nice watch. And these days, I wouldn't go and buy that again. I'm not even wearing it now. I still own it, and I'm wearing a, you know, this is $150 watch because it's just not where my head is at anymore. And if I tell you that, you already get a sense of what my priorities and my values are around money just from me saying that. And so what I think we need to do is go in telling stories, expressing values through just expressing our likes and dislikes, and then see how people respond to that. And you're going to very quickly learn who they are from their response to those things.

Love that. I take two big lessons away that connect with me from that. First, personally, I hate playing from a position of weakness. I just hate it. I would rather play my own game, and then, when the time is right, play from the top. And I remember something recently happened. My publisher was talking to me about a deadline. When is this thing going to be ready? You know what I said to them? I said, at this point in my career, I don't do deadlines. They were like, my agent got involved and all this stuff, and they're like, we needed to. I go, put whatever you want. It'll be done when it's done. To me, that is the ability to play from a position of strength. But when I started off, for example, my podcast, I knew I didn't have strength. I was a nobody. And starting the podcast, yeah, I had my own community, but I didn't know anything about podcasts. So I was like, we're just going to do it our way. When I hear your examples of if you play your own game, you're naturally playing from a position of strength. This is who I am. This is what I like. You're just playing your own game. The second thing I learned from what you said, and I love, is people are really attracted to a powerful vision. Someone who's really confident, has vivid ideas of what they love in their life. So when you say, you know, hey, this is what I love in my life, I would like to travel to these continents. It gets me really excited when I'm able to do X and bring my family to Y. Gosh. Whether the person agrees or not, I think a lot of people get inspired by that. So when you share that advice with your clients, what would stop someone from walking into a date and saying, you know, this is. This is who I am. Doesn't mean it has to be you, but this is who I am.

Feeling like you have no leverage. What? Let me put the question back on you for a moment. When you were able to say that to your publisher, like, at this point in my career, I don't do deadlines. And what you're really saying there is, I've built my own life. I'm not about to suddenly have someone from the outside dictating to me in this way. But what gave me.