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I'm In My 60s, and He Wants To Split The Bill While Dating

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The video addresses the ongoing debate regarding financial expectations during dating, specifically questioning whether men should be expected to pay for everything. The hosts argue that while traditional norms suggested men covered all costs because they were the sole earners in the past, this dynamic is less relevant today given that many people over sixty live on fixed incomes and lack significant disposable wealth. They emphasize that treating every date as a financial obligation can create unnecessary pressure and conflict, suggesting instead that couples should have open conversations about money before meeting to ensure they are on the same page. The hosts contend that assuming a partner will pay without discussion is just as problematic as expecting a woman to pay, noting that such unspoken expectations often lead to misunderstandings and premature rejection of potential partners. A key example shared involves a personal story where one host initially felt confused when his date insisted on paying for drinks, fearing it indicated a lack of funds. However, the situation turned positive when she framed her offer as an act of generosity rather than an obligation, which signaled to him that she was a true partner. This interaction highlights the hosts' belief that financial contributions should stem from a heart of generosity rather than rigid gender roles or societal "shoulds." They critique modern coaching rhetoric that ties feminine energy to receiving financial support, arguing instead that one's ability to be in their authentic self should not depend on another person's wallet. The discussion underscores that while some may desire a partner who can provide abundantly, the quality of the relationship and the spirit of reciprocity are far more important than who holds the credit card. Ultimately, the hosts conclude that there is no single right answer for everyone, but what works best for them is a system of taking turns and treating each other based on their current financial situations and levels of abundance. They explain that after several dates, they transitioned to splitting costs equally using an app, while still maintaining the option to treat one another as acts of love. They acknowledge that in cases of a significant income disparity, the person with more resources might naturally contribute more, but this should be a conscious choice rather than a default expectation. The video ends by urging viewers to prioritize clear communication about finances early on, as avoiding these hard conversations can lead to resentment and conflict later in the relationship, whereas honesty allows both parties to make informed choices about who they want to date.
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Should men expect to pay for everything? That's going to be our conversation today. So Paula, should men expect to pay for everything when it comes to dating? >> Maybe. >> What maybe? But that's not what we talked about earlier. >> [laughter] >> Likely not, but I think it is worthy of a conversation. >> Okay, so let's talk about this because this is a topic that comes up and I think it's uniquely different for those of us that are in mid life and I'm going to say for those of us over 60 where many people are on a fixed income, they're not, you know, as flush as they were in their 20s, 30s, 40s, or even 50s. So I think I I want to look at this at a couple different lenses. So traditionally it's always been men paid, but that was in a time when men earned all the money, right? >> Yeah, I and and women didn't earn any money. So there's that. >> So we got a fly here. >> [laughter] >> But you know, I I would say that women, I mean on some level, I'd say on an instinctual level, women might expect men to pay. >> Absolutely and I can't tell you how many forums and groups that I belong to that talk about that very specific thing and how women will reject a man who doesn't pay. >> They'll just reject him flat >> It's it is a common area of malcontent. >> Yeah, I would say certainly I've heard I've seen so many comments related to oh, it was such an ick, he wanted me to split the bill. You know, it was such an ick that you know, he wanted to split coffee, you know, that sort of thing. >> want to, you know, or not even like just he got his coffee and then I got mine. >> So so but when someone says he expected me to to split the bill, isn't that an expectation from another? >> It's no different from the expectation of the woman wanting the man to pay for the bill. It's an expectation, period. >> No, but if you're if you're going at it without any conversation before you're ever meeting, we operate with a lot of assumptions when stating. It's assumed man's going to pay, you know? So, I I know a dating coach who says a man isn't raised right if he didn't pay and a woman isn't raised right if she didn't offer to pay. >> Yes. >> So, so what This is the confusing thing is that most people don't talk about this before they ever meet. >> Certainly not on a first date and that's where the assumptions come into play. >> Yeah, and again, traditionally men are expected to pay and yet there's so much discord out there centered around that the man asked me to split the bill and there was an offense to it and I'll never see that guy again. And maybe that could have been resolved with a conversation in the very beginning. >> Well, so it it brings us to the question of why would you never see that person again? Are you expecting them to pay for everything? And where does that come from? Like I know some women who are desperate. Desperate and >> Financially speaking? >> Financially speaking and the problem with that is that whoever they're dating now becomes a fantasy reality, you know, a fantasy a rescue fantasy. >> Yeah, rescue fantasy. And by the way, for that person, whether it's a man or woman that expects the other person to, you know, contribute substantially to their life, if they never get that person, they have to take care of their own red wagon. Yeah, anyway. So, you know, and and here's the thing, I'm not here to And by the way, what we're sharing right now is our opinion. This is not a statement in fact. I'm not even suggesting there's a right or wrong in this. This is merely a conversation from both our vantage points because I know there are plenty of women who are very much expectant that the man pays for everything or pays for the majority of everything. In our relationship that's quite a bit different though. >> Oh, yes. >> And >> And I don't think >> oh, yes. No, no, you said that like there's something wrong. >> This was a conversation we had from the get-go. >> From the very first conversation. >> I will endeavor to share that you know, you and I had this conversation because I came from that world of traditional the man should pay and and you know, certainly on a first date they should offer. You know, and it there was a lot of shoulds. There was a lot of shoulds. >> What they say about shoulds? >> And yeah, and you um brought me over to the dark side. >> [laughter] >> I think I brought you to the light. So in in just to give you some context when before we had our first date, we had a 3-hour telephone call. Turns out about 2 hours into the call we had mutual friends. So we had this kind of I think that carried the conversation longer because of that. And but I said I well, first off I said can we not treat the first we have a fly here. Can we Can we not treat the first meeting as a date? Can we just be two people meeting and throw out all the pretense and expectations around dating particularly around gender expectations whether a man or woman. And in that I I told her that my philosophy in dating is to take turns with one another. It's not splitting the bill, but I like to take turns. Um >> Well, that's when we got into you know, what are we really talking about here? And I will say that my first reaction to you even having this conversation was you know, oh my gosh, does he have no money? Like I went I went straight there. And you know, you were just making a case in point. There was that, but I made assumptions around this that were not so. And it's so ingrained in us to think that if this doesn't happen, if A doesn't happen, then B or C. >> Yeah. >> You know, and the problem with going there is assumption. And the reality of it is I believe that you that that no two people are um have a given situation that's predictable. >> Yeah, I mean, here's the thing. What works for us doesn't necessarily mean it works for everyone else. We're just sharing a perspective so you can make your own choices. And really, I think in the topic of money, given that money is the second most common reason for divorce, I think it's naive not to be on the same page when it comes to money. What financial agreements do you create with one another to have a healthy relationship? Now, I want to tell you why I shared that with you before our first date. >> Yeah. >> So, um I get this goes back about 12 years ago. I had a first date with a woman. Um our first date was Halloween, by the way. >> Oh, fun. >> And we got dressed up and we went to a total dive bar. And and it was really fun and um and I remember paying I remember walking up to the bartender to get a round of drinks. And usually I just get my credit card. I I just kind of naturally take charge for the first date kind of thing. But I I looks like I I I guess I gave him cash and what happened was uh when it was time for another round of drinks, she pulls out her credit card and says, "I've got it." >> Okay. >> And I said, "No, no, I've got it." And she goes, "No, I've got it." And I go, "No, I've got it." Now, some people would argue that we got into a masculine pissing match, that she wasn't in her feminine. You know, I know a lot of feminine energy coaches would say that she was in her masculine, but what she did next floored the hell out of me. She put her hand on my arm, looked me straight in the eyes, and said, "Jonathan, I really appreciated that you treated for the first round of drinks. Will you allow me to show you my appreciation by treating you? Can you receive?" And I was like, first off, I'm I'm I'm in the Twilight Zone right now because I've never had a woman operate that way. And in that very moment, I go, "Oh my god, she's partnership material." Like, I didn't even That was all I needed to know because she operated from a place of generosity, not expectation. So, when we think of the title of this video, should and expect, I think those are two dangerous words in the English language when we come from something should be a certain way, and we expect it a certain way. >> So, um I we can maybe table this part of the conversation here for a moment cuz I know you want to get to some of these points, but it does bring up the problem with, you know, masculine divine masculine coaches, feminine energy coaching. And, you know, the idea that we can't be in our feminine energy if the man does not provide. >> Yeah. >> And Okay, I said to you something though initially, and I think and I think you actually agreed with me, which was >> Okay. >> that I can be in my feminine energy whether somebody's providing or not. >> You can be in your feminine energy whether he's in his masculine or his feminine energy. >> a choice. >> Yes, exactly. >> And for me, I read some of this stuff, and I think to myself, why would my feminine energy have anything to do with how he offers himself up? >> Yeah. >> So, you know, I just want to thank >> That's why I stuck my finger down my throat because I I vomit when I read so much of the content and rhetoric centered around this. And then when you and you bring it back up to paying and why this is such an important conversation. First off, as I said earlier in this conversation, for most of us in our 60s, many people are on a fixed income. There isn't a lot of extra disposable income to support another person. Basically, by the way, when you look at America, 80% of Americans still live relatively paycheck to paycheck and don't have a significant amount of extra resources to even cover them if they're out of work for a few months. So, I think it's naive to treat this cavalierly. Now, some people will say, "Well, Jonathan, if the man does the asking, he should pay." Well, when it comes to first date, men take the initiative because it's expected of us to initiate where we're going to go. That doesn't It's not even Again, this comes back to I don't believe the first time you meet someone it's a date, it's a meeting. Because you don't even know if you want to date this person. So, why is a man expected to Now, some will argue, "Well, women spend more money getting dressed up." And >> Okay, but I get dressed up if I were going out with my girlfriend. >> I know that argument pisses me off, you know, like >> Oh, I did my hair and I put >> did I spent $100 for a ham. >> Yeah. >> Well, I've seen women go on a date and walk out within 5 minutes, you know, you Did he get the Did he get the market value of all that dressed up? So, then there's the argument women make or men make more money than women. >> So, I think it's interesting that people in general now, in this current state of affairs, let's just say, you know, human pair bonding, is that um the idea that we are, you know, we come in I I used to say this to my kids. >> Yeah. >> We we come into this world with with one very important thing. We go out in the world with one very important thing, and that's our word. >> Mhm. >> You know? >> Okay. >> But to expand on it, it's also our virtues, you know? >> Our values. >> our honesty, our Yeah, all of that. >> And but at the end of the day, when you put us in a pine coffin, you know, the reality is there's nothing you take with you other than who you were in this world. It's not what you paid for in terms of >> Yes. >> And And I think what we're looking for in human pair bonding today is an ability to communicate with our significant other, an ability to have partnership, an ability for reciprocity and generosity that comes from the heart. And And in that, because we're all looking for that, there isn't anybody out there I think that's like, "Yeah, I want a complete, you know, dickhead." >> Yeah, yeah, [laughter] yeah, yeah. And by the way, you can have someone who pays for everything and be an absolute and you can have the kindest man in the world, but he's struggling financially. Which one do you want to choose? You know, here's where I I I want to put a pinhead because if two adults get together in a relationship, you know, one person's wallet should not determine the success >> Mhm. >> of the relationship. And we start with the very first date. So, it's such an ick when the guy says, "Let's split it." And maybe had a valid reason for it. You know, uh and then I get I see so much criticism if it's a coffee date. >> Yeah. >> As if it that's something By the way, our first date was a coffee date. >> Technically, yeah. >> Technically, it was in a nice restaurant and overlooking the marina at a hotel. >> Yeah, we Yeah, we We up Yeah, we had brunch. Uh >> And I lost my wallet. >> Yeah, [laughter] you lost your wallet. >> did lose my wallet. >> You didn't lose it, you'd forgotten your car. I think you planned that. By the way, I was going to treat anyway. But you know what I also say is I And I said this to you, um can I treat this time? Is that okay with you? >> Mhm. >> Because I I I wanted it to come from an understanding that this isn't coming from a place of expectation and obligation because to me, treating is a play comes from a place of generosity. And which is why I now I understand why a lot of women want that. They want to see is the man generous? Is he traditional? Does he signal intent? Um you know, does it it might allow the woman to feel more cared for. I can understand all that. >> Absolutely. >> But then But reciprocity is doing the same for him in my book. >> So, you and I had this discussion early on also that, you know, I believe it it And And we were talking about this from the standpoint of courtship, right? >> And um I you know, I think the reality of courtship today is that we're looking for men who are um that they lead to a certain extent. That doesn't necessarily mean they pay, but that they lead us, that they can strongly say, "I'm really digging you. I'd like to explore this further." That they can say, "Hey, you know, And I'm not talking like right away, but you know, maybe they plan a weekend, you know. >> Well, so >> And And I get not everyone is a right away kind of person. >> No, but what I'm But here's the thing. If you've gone out with someone four, five, or six times, there must be so If you're doing it with intent. In other words, if you're not doing it to get some sort of physical conquest, if you actually intend to you want a significant relationship, then I think there's nothing wrong with and I think a man and a woman should both equally say, "Hey, I like you. I'd like to explore getting to know you at a deeper level." This is what's often times missing in these conversations. There's so much fear around going deeper. We weren't afraid to have this conversation before we ever met. We had a brief conversation. Then I want to say by the time we were physically intimate, maybe it was before that. We talked about where we stood financially. In other words, kind of gave a picture of our net worth and where our income comes in and how we plan for the future. We had these conversations because quite frankly, it is so naive not to have these conversations. And by the way, please forgive the the the illustration I'm about to say, but before that penis goes inside the vagina, which is my rhetoric, then this these are important conversations to have. >> Yeah. >> And I don't know why there's so much res- What's the word? Res- When you're trying to resist something. Not resistance. Uh Oh, god. It's an R word. Anyway. Re- reluctance. We'll say reluctance to have these conversations. >> Mhm. >> So So, coming back to should men expect to pay everything? I mean, flat out, I don't think that should be an expectation unless you're dating someone who has significant abundance. Significant abundance. So >> Somebody up at the top said >> Here, I'll do it. >> Duh, yes, they should. >> Duh, [laughter] yes, they should. Okay. Um you know, again, that's kind of but from a man's perspective, I don't want to be with someone who treats it as an expectation, as if it's an obligation, because then you might as well say then I'm I I can have sex whenever I want. >> So, there's >> Now there's the I'm not saying that's the exact same argument, but >> There's but there's a whole camp out there that believes that the man should pay and that if he's not, he's not allowing you to be in your feminine receiving mode. First of all, and that and the ick comes from that, you know, is he just um uh you know, wanting to just I mean, he's he maybe he's got a hundred dates, you know, and and and you're just not that special. >> All right, well well wait >> And that's all right. Hey, I didn't make this up. This is the camp that I >> Okay, by the way, can we agree that 99 out of a hundred times in today's environment, we are going out on dates with total strangers? >> Absolutely. >> most of the time. Maybe let's just say nine out of ten times. I'll say nine out of ten times. Sure there's people that meet out in the wild and that sort of thing. And some people will argue that a coffee date represents low effort and no interest. Well, first off, it might take being with someone two or three or four times to develop interest. >> Yeah. >> Um I've had dates where we walked on the beach. I've had dates where it's been in a park. I've had dates I'm like, why or excuse me, I've had first meetings, let me clarify that. First meetings in places like that because you're just doing the sniff test. You're doing what two dogs do when you know, when we walk the beach and two dogs come up and they go >> [laughter] >> Oh, what's your perfume, by the way? So, that's what a first meeting is. It's a sniff test to see if there's even your pheromones align with one another. I think the problem is when we create these grand expectations. Now, I know some people will argue that what we're sharing is absolutely wrong. >> And it goes against everything they've >> Everything they've ever learned and taught and some people will say we absolutely agree with you. I'm here to say you've got to make those choices for yourself. This isn't we're just sharing with you our perspective and I'll I want to go a little bit further. Our first meeting, I treated. Um the second time we got together, we just had drinks at your place, so it didn't count as anything. The third time we got together, I said I want to take you out on a fancy date. >> Yes. >> And by our fifth date, uh you took me to a really expensive a really high-end sushi place. I mean, it's probably commensurate to the the dinner we had a few days before. And ever since then, we've taken turns and now that we live together, we use an app called Splitwise. We actually we contribute equally to the rent. >> Yeah, the home is, you know, >> The home is kind of like um we we split that equally. The The app is basically you put in the amount and you you settle up at the end of the month kind of thing. Um but then there are nights where I go, "Hey, sweetheart, this is my treat." >> And I do the same. >> And she does the same. That's when we show our generosity. Um and this is what works for us. I mean, it may not work for everybody, but this is what works for us and what feels fair. Now, by the way, we are pretty close to equal from our financial resources. She has a little bit more in the bank than I do. I generate a little bit more income on a on a on a day-to-day basis than she does. So, we're commensurately close. I know this gets to be radically challenging when there's a gigantic mismatch. And and I prefer the person who makes the most contributes the most. >> Do you? Really? >> Who makes the most. >> You think the person who makes the most should contribute more? >> Yeah, the person like I you know, I was thinking like my my my wealthy friend, you know, he makes the most, he contributes the most. You know, but but if but if you have for example, if you have someone who makes a quarter million dollars a year and someone who makes eighty-thousand dollars a year. The quarter million >> But the quarter of a million dollar person might have been divorced, owe someone alimony and child support. I mean, you don't know what >> Well, then taking all that into consideration. >> Then what? You're going to sit there and do, you know, assets and liabilities? I think generosity comes from the heart. >> All right, let's say somebody makes a half a million dollars a year and doesn't have alimony and all that and he's dating someone who makes eighty-thousand a year. >> Yes. >> And by the way, if it's a woman who makes you you have a friend who woman who makes close to a million dollars a year. >> Yeah, so but here's the question. Does any of that really matter or is it a matter of what is your um spirit of generosity in the relationship? >> There's no doubt. >> What is your sense of what you want to what you want to contribute into the relationship, not only your emotions and your heart and those things, but you know, do you put your money where where your mouth is kind of thing? >> So, I I said what I said a moment ago because if I had twenty million in the bank, I'd cover everything for us because I have the abundance. >> Sure. >> I think the person who has abundance and comes from that place probably and the other person doesn't have it, they should contribute the most. That's where I'm coming from. So, coming back and we're going to put a bow on this. Um should men expect to pay everything? I don't believe that's the case that should expect everything. But I certainly uh subscribe to um you know, I think traditionally we're raised uh for initially making that investment, but I think right off the bat have a conversation, see where two people at because if you're not on the same page, you're going to have conflict later on down the road. >> So, at what point do you feel like that conversation needs to be had? >> The minute [clears throat] you start to spend money. >> So >> Maybe before you meet. By the way, I I subscribe to having hard conversations before you meet. You know, why what here's the thing. I hear too many people complain after the fact that they found out all these things that they would have said no to right from the very beginning. All right, those are our thoughts. We'd like to hear your thoughts. Post a comment below. Let us know what you thought about this, if it resonates with you or not. As always, if you find value in these videos, please hit that like button. Please share this video. 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