Submitted by ThrowRAPotential5 t3_1282x6q in relationship_advice
So I've been dating a guy for around 3 years and he is horrible with his money. He is 40 in August and still ask me/his mum/best friend for money all the time. He doesn't have a car either so he regularly borrows mine/his best friends and is currently living with a kind and wealthy family, who is allowing him to stay in their pool house until he gets on his feet. He was homeless before then.
He isn't lazy and actually works all day. However he has habits that prevent him from saving anything and if I am honest I think he has gotten used to receiving help from others. So his relationship with money and "taking" isn't the same as most people. I met him broke so this isn't necessarily a deal breaker for me, But the problem is that he is beginning to steal from me. There have been more than one occasion that little things have mysteriously 'gone missing' from my car/bag when he is around (like my spare house key, library card (weird I know) and letters), the other day when I was driving him to work, I caught him going into my bag and taking out my A5 diary and quickly putting it in his pocket. He did not look at the book when he took it, so I am thinking that he thought it may be my purse. I didn't say anything.
In addition to this, he has NEVER paid me back any of the loans that I have given him although he always promises to. The last loan, which was a moderate loan of $600, he attempted to gaslight me when I asked for it back and said that I had never given him money before. Which was really strange. Before you judge him, he is a great guy otherwise. But his money woes are causing him to act out of character, and his closest (which includes me and his best friend) are getting the brunt of it. He recently had a huge argument with his best friend because his best friend asked him to put a little petrol into the car he let him borrow for the week. Which made the guy i'm seeing furious, because his friend usually fills the tank.
I think the guy I am dating won't learn a lesson unless I stop being generous, AITA if I stop giving my money away and actually make him pay me back, even though I am aware of his financial woes. How can i get him to stop stealing?
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