What should I do in this situation?

okay I have a friend who I have been knowing since last year. I wasnt all that interested in him, but in the past three months we have grown closer together. There have been instances where he has been kinda flaky toward me, like when I had gotten a boot on my car, I had asked him for 100 dollars to get it taken off he had told me that he couldnt do it. because he didnt have any money. then there was an instance where we were supposed to go out, and he had told me that he would buy the tickets for the event that we were going to. The day of the event he told me that he couldnt pay, he asked could I pay and then I pay him back. Well fast fowar to now, he is out of town, and he doesnt have any money for a flight to get back home, and he claims that he left his debit card back home. Some girl was house sittin for him and he said that he couldnt ask her because, he did not want her to know where his private things were. So he's asking me for 350 dollars for a flight back home. i personally do not like to see people in a bad situation, but I feeli like he will not pay me back. Should i give him the money or should not. You guys can be harsh I need real truthful answers.