Anonymous
Post 06/02/2026 09:42     Subject: Restaurant Checks

You don’t mention if you’re in a heterosexual relationship but I will assume you are and you are a woman. Would you feel the same way if you were the one making more money? I seriously doubt it. Women want equality only when it’s convenient. Now go sign up for the military selective service.
Anonymous
Post 06/02/2026 09:09     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:Anyone else find this joint entertainment account weird? I mean, it's not a horrible idea or anything, but I have never heard of anyone doing this.

So I want to know how this came about. Was there tension over who was paying for dates?


Very weird for this non married set up… Ugh


I explained earlier how it came about. Why the Ugh? If you’re in a committed long term relationship, why not enjoy the benefit that married people have to not be concerned about which of you is going to pay for dinner?


Because you're not married. Plus it's not working as she/he is cheap.
Anonymous
Post 06/02/2026 09:06     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:Anyone else find this joint entertainment account weird? I mean, it's not a horrible idea or anything, but I have never heard of anyone doing this.

So I want to know how this came about. Was there tension over who was paying for dates?


Very weird for this non married set up… Ugh


I explained earlier how it came about. Why the Ugh? If you’re in a committed long term relationship, why not enjoy the benefit that married people have to not be concerned about which of you is going to pay for dinner?
Anonymous
Post 06/02/2026 06:38     Subject: Restaurant Checks

Anonymous wrote:Anyone else find this joint entertainment account weird? I mean, it's not a horrible idea or anything, but I have never heard of anyone doing this.

So I want to know how this came about. Was there tension over who was paying for dates?


Very weird for this non married set up… Ugh
Anonymous
Post 06/02/2026 00:39     Subject: Restaurant Checks

Brother, just quit the "they" and say it how it is: you are broke compared to her, and she resents you for being poor. She wants at least the illusion of being "treated" by a gentleman who is her equal.

You may be hanging on to her, but you resent her too and feel belittled. This will not end well.

~ an estate attorney (F) who has seen plenty of family dynamics
Anonymous
Post 06/02/2026 00:23     Subject: Restaurant Checks

Anonymous wrote:I am in a long term committed relationship (3 years so far); we love each other very much (as in ‘til death do is part). Each of us are in only our second serious relationship, after tragically losing our spouses of multiple decades.

In our marriages, finances were joint, and it never mattered a whit who paid a restaurant bill, from inexpensive to lavish, because everything was from one pot. Now in this relationship we have separate finances but a joint account to pay for hotels and restaurants. However, my partner, despite significantly out earning me and with a higher net worth, doesn’t like it when an expensive meal goes on the joint card — they want to be treated.

This is a source of sporadic tension. I like things to be as fair and equitable as possible. They just like to be treated. Well doesn’t everybody? I’m not sure how to prevent these flair-ups, but consistently picking up big checks for my richer partner is not sustainable. And talking about it is unpleasant and ruins the mood.

Has anyone out there successfully navigated this kind of situation?


Joint account and you're not married? Why on earth would you ever do that?
Anonymous
Post 06/01/2026 22:18     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:OP here: my partner was raised on perhaps the largest estate on the most prominent point of the richest island in the USA. But they say they are by no means to the manor born. Go figure.


[/b]So you are definitely a man and she’s the woman[b]. You mentioning your love language being taking care of the repairs and cars also reveals you are a man.

Why are you dating the heiress ? Date a fellow teacher take her to McDonalds and be happy


Do you know me? I was to the manor born myself. And the best car repair place I ever have been was run by lesbians in Cambridge MA. So where am I revealing sexes exactly?


NP. Male, female, or NB, you're a bit tiresome. Stop yapping about "to the manor born." Have you fallen into genteel poverty? Do you now work as a tutor or governess to a cruel widower whose wife died under suspicious circumstances? We're not living in Victorian England, friend.
Anonymous
Post 06/01/2026 21:55     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:OP here: my partner was raised on perhaps the largest estate on the most prominent point of the richest island in the USA. But they say they are by no means to the manor born. Go figure.


[/b]So you are definitely a man and she’s the woman[b]. You mentioning your love language being taking care of the repairs and cars also reveals you are a man.

Why are you dating the heiress ? Date a fellow teacher take her to McDonalds and be happy


Do you know me? I was to the manor born myself. And the best car repair place I ever have been was run by lesbians in Cambridge MA. So where am I revealing sexes exactly?


OP, what is the point of being cagey about this?
Anonymous
Post 06/01/2026 21:36     Subject: Restaurant Checks

Anonymous wrote:I’m guessing your partner is a woman, because if genders were reversed it would be completely absurd (higher earning man wanting to be taken out all the time).

I am a woman, 50s, with higher earnings and NW than my boyfriend. He does well by most standards but I had a high earning career and my ex did well too so I don’t have alimony and I share child support (unlike him), so I’m all around in a better position. I wouldn’t call us LTR yet (a year but still “dating,” haven’t had the talk or anything). But we take turns paying, and I try to get the more expensive ones without making a show of it. I would not be pleased in your shoes.

That said, my BF does other stuff to make me feel taken care of and appreciated (like always brings me coffee in bed, helps me with stuff in my house, would carry heavy stuff for me if I needed it, etc). Who pays for dinner or even travel is a total non issue because I can afford it and I want to spend time doing these things with hik with him and he does other things that matter more to me than money.

If you are doing those things and sh still expects you to pay just because you’re the man, she doesn’t sound like a catch.


Gay couple.
Anonymous
Post 06/01/2026 21:31     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:I am in a long term committed relationship (3 years so far); we love each other very much (as in ‘til death do is part). Each of us are in only our second serious relationship, after tragically losing our spouses of multiple decades.

In our marriages, finances were joint, and it never mattered a whit who paid a restaurant bill, from inexpensive to lavish, because everything was from one pot. Now in this relationship we have separate finances but a joint account to pay for hotels and restaurants. However, my partner, despite significantly out earning me and with a higher net worth, doesn’t like it when an expensive meal goes on the joint card — they want to be treated.

This is a source of sporadic tension. I like things to be as fair and equitable as possible. They just like to be treated. Well doesn’t everybody? I’m not sure how to prevent these flair-ups, but consistently picking up big checks for my richer partner is not sustainable. And talking about it is unpleasant and ruins the mood.

Has anyone out there successfully navigated this kind of situation?


OP is a man dating a wealthier woman who expects to be cared for. Good luck.


It sounds like she cares for him quite a bit and wants some reciprocity.

If OP was female people would be saying he's a gold digger.
Anonymous
Post 06/01/2026 21:17     Subject: Restaurant Checks

Why are you being so coy about the gender? What is the point of hiding it?
Anonymous
Post 06/01/2026 20:23     Subject: Restaurant Checks

Anonymous wrote:OP here: my partner was raised on perhaps the largest estate on the most prominent point of the richest island in the USA. But they say they are by no means to the manor born. Go figure.


oh fun, riddles!
Anonymous
Post 06/01/2026 19:20     Subject: Restaurant Checks

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:Do you both have kids that you plan to leave your assets to?

This is something that needs to be tackled head on. If you are really permanent, you either need a joint budget that covers everything and agree how to fund it (maybe with exceptions for birthday/christmas/anniversary) or you set some limits and live within them. If she decides she wants someone with more money to “keep up” that’s on her.


We both have kids and no intention or need to leave money/assets to each other or each other’s kids. We don’t need a joint budget for everything; we maintain separate households. We just need to solve our T&E budget/funding.

I think it upsets my partner and makes them feel bad about themself whenever they find themselves wishing I could 100% keep up with them. Because no two people are exact equals in this regard, and married people don’t struggle this way.


I asked about kids because ultimately, they are affected by this. Your partner may feel like if they overspend on you that is money taken from their kids. And their kids might also have feelings about that. Conversely, if you overspend, you will have less to leave your kids.

There is no easy way around this. You both need to talk about how much you are willing to spend and what you are willing to forgo. If something isn’t in your budget and is important to them, they can treat you or enjoy it alone, or maybe your relationship isn’t meant to go the distance. And conversely, if they think you are being cheap on something you can actually afford, you need to consider that - is it worth the extra money to maintain this relationship?


OP here: This is so true. The stress I feel keeping up with my partner’s spending is largely about the erosion of my estate, which will go to my kids. My partner’s kids are all loaded, but they feel an obligation to never touch their capital (a very old-money hangup, where you are supposed to be rich while only spending the interest on your interest )



I was with you until this comment, but this isn’t a hangup, this is smart. This is how generational wealth stays generational. That was an article in the WSJ today about a seminar that children of the wealthy go to to learn to be good stewards, and they used the Vanderbilt family as an example of a fortune misspent. Ultimately if this is going to work you both have to set your limits and live within them, compromises and all. If that doesn’t work, you aren’t meant to be.
Anonymous
Post 06/01/2026 19:17     Subject: Re:Restaurant Checks

Anonymous wrote:Can you agree on funding that account pro-rata your earnings post tax and post obligations to other parties ?

If this is a lifestyle issue (eg the partner considers expensive restaurants a waste) then you shouldn’t be with them at all. This is very hard to overcome


Agree that disagree and break up. You can each feel nd a better suited match.
Anonymous
Post 06/01/2026 19:16     Subject: Restaurant Checks

Anonymous wrote:I think you should quit saying how happy you both are and how this relationship is "forever". It sounds like you are both having resentment about this issue for opposite reasons.

I'd like to know how the joint account is funded. Do you each put in $1000? Or does your partner put in $1500 and you put in $500 because they earn 3x your income? It seems like just funding the account is going to lead to the issues you're trying to avoid.

Your partner wants you to spend beyond your budget because they want to enjoy entertainment equivalent to their income. Just going to Bob's Bar & Grill instead of the fancy steakhouse isn't going to solve this issue. They want the upscale dinner and it sounds like they want you to pay for it all.

Probably because they have tallied up the value of hotel and travel expenses that they are covering from points and other perks. And they probably push for the $1000/night hotel when you might have chosen the $200/night option. So even if you pay half, you are still straining your budget.

I don't think they "love" you enough to want to carry you, in order for you to join them in their more expensive lifestyle. If you are paying half and sometimes all, they don't have to face the fact that your wealth class is a notch or two below them.

And they aren't looking at your income/expenses spreadsheet to see how much this is stretching you thin.

You are dating for now and with kids (even adult kids) on both sides, getting married would be a mess financially.

I'd bet if they were writing about this issue, they wouldn't be saying they know that you two are going to be together forever.

Something is going to break soon - either you say you've reached your financial limit and can't pay for more. Or they are going to be resentful that they are putting so much more cash into a dating relationship where they have nice tastes and an expectation that you should share the entertainment expenses equally, or even that you pay a little more because they have *reasons*.

Have that talk now, even if it means they decide they can find a future partner that can equal them in affording travel & dining expenses.



This is a read 🔥