It is hard when someone asks you for money - I have been burned a few times, unfortunately..
Most for small amounts ($100, $200, etc), but the largest was for $1,300 which I gave to a 'friend' who really need to get out of a bind... never have seen the money since... and I don't think I will, as eventually he was arrested for stealing money from credit cards...
BUT, in other cases, I have given money to various friends, who have paid me back, some took a few years, but they gave me what they had until they had. One whom, eventually gave $2,500, has paid me back almost everything, and he will give me the rest in a few months. It felt good to help someone who really needed it...
It is a touchy situation... and sometimes, people will burn you..