Loaning money based on emotion is not always good

[theking]

‘I feel like a fool’: I loaned my friend and former lover $50,000 to help her buy a home — now she’s treating it as a gift

‘I gradually put $50,000 into her bank account so she would have that cash cushion ahead of her interview with the co-op board’

I had a fling with a very nice woman about two years ago, and we became friends. She was not interested in a relationship with me, which was disappointing at the time and, even though I loved her and wanted her to love me back, I respected her decision. A few years ago, she took advantage of the low interest rates and bought an apartment with a 3.5% 30-year rate. I gradually put $50,000 into her bank account so she would have that cash cushion ahead of her interview with the co-op board. They accepted her, and she moved in.

The problem: She has continued as if the money was a gift. I have brought up the fact that I would like her to repay the money — as agreed at the time — and she said she’s doing her best. But the more time that goes by, the more I have come to realize that she has no intention of ever paying me back. In a worst-case scenario, the loan will need to be written off as bad debt; assuming that happens, how do I account for that on my taxes? I feel like she had no intention of paying me back, although knowing her that’s hard to believe.

In the meantime, how can I persuade her to repay me the $50,000?