If You Were Going Out With ?

If I were just dating someone (or living with them), I would not, under any cirstances, lend that kind of money to him or to his siblings. You would just be giving the money away -- you most definitely shouldn't expect to get repaid. If your partner is trying to manipulate you into doing something you don't want to, then you should break it off. He or she does not have your best interest in mind, and this is not something you should have to live with. You need someone who will allow you to make your own decisions and not try to use your relationship and feelings for them to coerce you into things you don't want to do. Not to mention that you shouldn't have to fund someone else's lifestyle. You need to be concerned with your own well being and finances. If you loaned them the money or continue to give them money, you will most likely never see a dime of it back. And that's a good chunk of money you're talking about.