OP, I had a friend whom I met in my first part time job when we were both sixth form age. Over the years, our lives went in different directions but we remained fast friends. We always had so much to talk about and she was always so kind and (I thought) generous.
I studied and worked really hard and in my thirties, I landed a fab job and my husband and I bought a lovely home for us and our kids. I think it was at this point that my friend became grabby. I think it was because she could see with her own eyes how well I was doing.
I’m trying not to denigrate her lifestyle, but it was so different to mine and, as we both had children, the divergence in our ideals and choices just became more and more obvious. But still, we retained something of a friendship. Only… she kept asking me for money. Repaying small amounts and then asking for more.
It never prevented me from paying my own bills, because I was in a very fortunate position. But, at the end, she owed me £500 - like yourself.
By this stage in our lives, I had a lot of “home truths” I wanted to share with her. About money, school attendance, drugs, kids, boyfriends… it was all just coming from a place of wanting my recompense. A pound of flesh in place of my hard earned cash. Worthless words!
I wrote the money off and said nothing. It was the strongest message.
First she messaged me asking for another £20. Ignored. Then again. Message more desperate now - about her kids and bailiffs. I ignored this too. A few days later she messaged to ask me over for coffee. I responded and said yes and she asked me to bring her some cigarettes when I came. So I ignored and didn’t go.
A few weeks later she sent me an apology and £70 to my bank. I still ignored her. That was the last I ever heard of her.
I walked away from that decades-long friendship £428 worse off. But I could still be “friends” with her now, and owed £3,000 if I hadn’t wised up!
My story is supposed to demonstrate that the best way to deal with this is to write the money off and say nothing. No words will actually make the blindest bit of difference. And, the longer you keep this line of communication open, the more open to manipulation you are.