My brother-in-law expects my husband and me to pay for his food every time we go out. How can I tell my husband I don't want to do this anymore?

By Aditi Shrikant

'We also pay for the daughter's food and drinks and she doesn't usually even eat half of the meal'

"One time, both mother and daughter ordered the most expensive dessert at about $16 each only to eat half of one and left the other."

Dear Dollar Signs,

My brother-in-law is a lovely person. So very kind and sweet. However, no one is perfect. His second wife is the problem. Since he married her he is always broke. They both have steady jobs in public services - normal, working-class people like me and my husband.

Everytime we meet and have a drink or a meal with them (even if it's their invitation) we end up paying. So much so that I don't want to socialise with them anymore. My husband, on the other hand, does. And yes, he ends up paying.

We also pay for the daughter's food and drinks, and she doesn't usually even eat half of the meal. She is one of those kids who picks at their food. One time, both mother and daughter ordered the most expensive dessert at about $16 each only to eat half of one and left the other - that kind of waste.

We don't feel it's right for them to use us like this as they are probably more solvent than us. But we also don't feel right to say anything. For me, I just avoid them. But I can't ask my husband to as it's his brother. How do I ensure that my husband doesn't keep on paying?

Annoyed

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Dear Annoyed,

Sibling relationships are hard to understand and impossible to alter. The norms between your husband and his brother were cemented far before you entered his life. He has likely dealt with and even enabled this dynamic since they were children, which is why he is either unwilling or unable to find a way to push back.

Even if your husband commiserates with you, I wouldn't assume that he is as bothered by his brother's actions as you are.

Families are systems and your husband's behavior probably helped that system run smoothly. So while he might know that his brother's expectation that you pay for meals out is unreasonable, the cost may be worth it to him, if only to avoid disrupting the system.

I would have a straightforward talk with your husband about what you'd like to change going forward. Be honest, concise and positive. You could start the conversation by saying something like "I want to be able to enjoy time with your brother and his family, but that means we need to set some boundaries when it comes to how much we are spending."

You, very understandably, are worked up about how much food is ordered and goes untouched. I get it, but I would leave that out of the conversation.

Litigating the past is rarely productive and might even be unfair. You could be assigning more intention to your brother-in-law's actions than exists, says financial therapist Amand Clayman.

"The person didn't know they were digging this financial karmic debt with you," she says. "For all they know this is something you want to spend money on and it's a value of yours."

I also wouldn't get into what you think of your brother-in-law's wife. Even if you did like her (it sounds like you don't), the issue is that you want these meals to feel more equitable.

A worthwhile compromise might be to tell your husband that you'd like to set a limit on how much you both are spending at these dinners. This way, he doesn't have to confront his brother about paying but you also have some control over how much you are spending on these meals.

You could also let the check sit on the table before reaching for it, Clayman suggests. "Wait to see if someone picks it up," she says. "Yes, it's going to feel endless, but you never know. This person might be open to picking up the check but you swoop in so quickly."

You can also simply tell the server that you'll be splitting the check down the middle. This would require your brother-in-law or his wife to vocalize a different desire, which would be quite bold. You can also suggest you all do different, less-costly activities like going to a park or grabbing ice cream.

You and your husband just need to agree on how much money you want to spend on your brother's family. Then, pick activities that fit within that parameter.

Understanding their dynamic doesn't make this experience less annoying. Feeling like your generosity is not being reciprocated or even appreciated is frustrating. But if you focus on what you want to happen going forward, as opposed to the personalities at play, you might be able to come up with a solution that leaves everybody comfortable and saves you a bit of money.

Write to Dollar Signs at dollarsigns@marketwatch.com.

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-Aditi Shrikant

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09-17-26 1508ET