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

The good news is you don’t have to have an awkward conversation, writes advice columnist Eleanor Gordon-Smith. You just need to stop paying

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.

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