If you have to ask the internet if you should lend your boyfriend money then you shouldn't loan him money. If your boyfriend doesn't have a job you shouldn't loan him money or let him move in. If you can't afford to loan him money, or you have kids, you shouldn't loan him money and he shouldn't have asked. I generally go with a gut check when someone asks me for money. I've loaned out a few grand on several occasions and always got it back in short order. I've chose to not loan out a few grand to some friends, later on at least one of them said that I probably made the right choice. In the first year of dating my wife I loaned her a hefty amount and she promptly repaid, I think it was a good early trust building thing to do. Loaning money to people who won't pay it back can be a great way to get rid of people you don't want in your life but are having a hard time shaking off. Just ask where your money is every time you see them and they will stop coming around.