OK, I am in kind of a sticky situation and I would love your opinion! I have been dating my boyfriend on and off for a little over a year. Our relationship is not great, but it is good enough. We are very comfortable with each other and get along for the most part. We are both students, he works, I don't. A couple of months ago, he told me that his family was having financial problems and that they were calling him every month to borrow money. In total, they have borrowed about $3,000, if not more. He told me that because of this, it has dried up his savings and he asked me to loan him $300 to help him cover Fall tuition. Now, I have a few reservations about this. My first concern is that he might not give it back to me. He is a frivolous spender. For example, last Friday night, he went out to the bars and a strip club with a couple of his coworkers and spent almost $300. Tonight, he wanted to go out again with the same coworkers, but I refused to drive him to his coworkers house because he did not consult me when he made the plans to go out with them tonight. (I have a car that my parents gave me, and he does not have one). I have been very generous with allowing him to use my car whenever he wants it, but I told him I would not let him drive if he was planning on drinking. My other concern is that I do not work. My parents support me financially because I am a full time student and they do not want me working while I am getting my degree. Whatever spending money I have is what my parents give me each month. I have enough in my savings to cover him and my credit card bill for this month if he cannot pay me back, but I do not want to get him in the habit of asking me for a loan when he is in a tight situation. I do not want $300 to come between us because it is such a petty thing. I was reading other posts about friendships that were ruined because of money and I would hate for this to happen. What are your opinions?