You know the answer bud. You have to say NO because these friends of ours are just using us as an option even if they have another greater option. You have admitted that you're not ready to loan him and you have taken your want away instead of taking them close to you with that money of yours. You've sacrificed for how long and then there's this guy will approach you out of nowhere trying to loan you some money. Just say politely that you're not going to lend him some money or if you can give him a little portion of your spare money that you're okay in not getting paid with it so you just can get rid of him trying to ask you once in a while. I've been there and done that, they're quick to ask money but when you ask them to pay money, they're turning into dust and gone in the wind.