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I often offer to pay, but one friend is becoming over-entitled. How do I talk to her?

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About a year ago I married my long-term boyfriend. Due to his financial situation, my life has become a lot more comfortable. I feel a sense of responsibility to help my friends or family – offering to help them pay their mortgages if they want a career break, or paying for a holiday – and while most friends are gracious, there is one in particular who is becoming over-entitled.

She moved into my old flat and pays reduced rent. She has a job that pays fairly well, but when she mentioned she wanted cosmetic surgery, I offered to lend her the money. She asked if she could stop paying rent for a few months instead, which I agreed to. For her birthday I offered to take us away, and she picked an expensive hotel. I refused, as I wouldn’t have enjoyed it, but she keeps bringing it up.

I’ve noticed that I want to spend less time with her because I know I’ll have to foot the bill, which is awful. I need to have a conversation with her about it, and I’m not sure how.

Eleanor says: I don’t care if you’re Scrooge McDuck and you sleep on a giant bed of money, your friends don’t get to start treating what’s yours as though it’s theirs. This is a basic courtesy for all kinds of things: money, time, energy, hospitality; when a friend gives you something of theirs, you don’t act like it was yours to expect all along.

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This is true even if it was yours to expect all along. You still have to ask if it’s convenient to stay the night, even if you’ve stayed a hundred times before, and even if you’d be slighted if they said “no”. Anyone who recognises the edge between “yours” and “mine” knows that a gift – even an expected one – still has to be treated like a gift.

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So why doesn’t your friend get the distinction between “yours” and “mine”? I think that’s key to understanding why she’s behaving like this.

Is it possible she experiences money in a completely different way to you and is making the rudimentary mistake of assuming that other people’s attitudes mirror her own? I think we’re particularly prone to make that mistake about money. I’ve had boyfriends ask me to access my retirement savings to spot them between paycheques, and I’ve had friends ask me for the $1 they spent on a group video rental. Both thought their attitude to money was the only reasonable one and that everyone else in the world presumably shared it.

Does your friend think money is just fun and frivolous? Does she think she’d spend the same on you? Does she relate to this money as everyone’s good fortune? Does she think the boundary between “yours” and “mine” just should be porous in a friendship, such that it hasn’t occurred to her you might feel disrespected by that porosity?

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I think there has to be something like that bedrock disagreement about “yours” and “mine” going on. If she was just trying to drain you dry I’d expect her to be more strategic – surely any real money-grabber would know she’d only irritate her target by rapping her watch and asking where the cash is.

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The good news is you don’t have to have an awkward conversation if you don’t want to. It is very difficult to persuade someone that their approach to the yours-mine boundary is wrong – especially with money, and especially in close relationships. (“But what’s mine is yours!”)

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Instead, all you need to do is stop giving her money. In that way, you share a blueprint with all the other ways we find ourselves giving more of something valuable than we mean to – money, time, attention. Your only goal is to stop giving it. Just don’t pull the card out when the meal ends: “forget” about a big ask; simply say, “I don’t think that’s going to work.”

Be prepared to endure the silence without feeling the need to fill it with reasons. Let her force the issue if she wants; that way the burden on her is to explain why she’d like more, not on you to explain why you’re making a change.

This question has been edited for length.

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