My advice....don't loan anyone money you can't afford to give away. I have in laws that owe us thousands. So now we're the a--holes for asking/expecting it to be returned when we could've started out as a--holes for not loaning to them in the first place...but we wouldn't be out any $.
I'd dump your boyfriend but not because of the money issue....because he makes you miserable. Consider the money tuition to the school of hard knocks...
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