So here's my dilemma (I'll try to fill in most of the blanks): My fiancee's older brother is a loser (and no, there's not really a nicer word for it.) In the two years I've been with Brian, his brother has obtained and lost about fifty jobs, and two or three apartments. For the last several months, he's been bouncing around from his parents' house to his sister's house to homeless shelters... But still smoking cigarettes, still smoking pot (which means it's harder to get a job... ugh), still driving around in circles burning up gas, all of which is funded by his parents and his sister. The situation is bad enough that we're loaning his parents money to pay their bills because they keep giving the brother money. Last night, he called us to ask if he could stay here and then borrow some money. Luckily, Brian wasn't here, so it was easy for me to weasel out of. But now, he's on his way over here to borrow money. My fiancee, in a show of valor, lol, left, saying "There's a grocery store gift card on the table if he shows up." He's too nice to tell him to get a job. At this point, I'd like to tell him myself. Is this horrible? Should I wait for his own family to say it? I feel like they're enabling him to never straighten up. I mean, Brian and I are 22 and 19, and both work full time jobs. The brother is 30 and still pretending he's a kid. What do we do?