Ex boyfriend owes me money and keeps saying he's broke so he can't pay me back. How should I handle this?

He keeps promising he'll return it but it's been a month now and he keeps going out drinking and doing god knows what so he never has any money left to give me... I don't want to continuously be asking him for money... if it was a couple hundred I wouldn't care but he owes me more than a thousand...
I feel like this is a lost cause. Anyone have any ideas? Thinking of giving up but so angry at myself because I trusted him with my hard earned money...
Ex boyfriend owes me money and keeps saying he's broke so he can't pay me back. How should I handle this?
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