Philippa Perry

Philippa Perry

Watching someone make the same old mistakes

It tries your patience

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Philippa Perry
Aug 27, 2025
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Dark Matter, Cornelia Parker

Write to me at AskPhilippa@yahoo.com Subject to Terms and Conditions

Hi Philippa, My sister is having a really hard time and I want to be there for her, but I am finding it difficult. She is in the middle of a separation and divorce, has a young child, lost her job and is under huge financial pressure. All of that deserves sympathy, and I do want to give it, and yet…

What I struggle with is the way new details keep coming out. Week by week I learn more about how much she knew at the time: that her partner was not pulling his weight, that she was spending her inheritance while hiding how bad things were, and that she went ahead anyway. It feels like she expects everyone to clear up the mess while joining her in saying how awful he is.

This is not the first time. For years she has been in relationships with men who are violent, manipulative, or irresponsible. When she inherited some money, I hoped she would use it for security. Instead, she spent it on a wedding and soon after was pregnant. Within a year the marriage was over, the money gone, and debts piled up in her name.

Now she is devastated by each new disappointment, while the rest of us are weary rather than surprised. My family are helping with childcare, legal fees, and bills, but she often accuses us of not understanding what it is like for her. I know I do not, but I do know how painful it is to watch her repeat the same patterns.

We all want to support her, but not with money that disappears, and we fear she may become homeless again. My question is: how can I feel more empathy for her while also recognising that some of this comes from choices she keeps making?

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