Friends and money are typically two things that do not mix. If it is not a gift, there will be trouble...been there, done that. JMHO.
Lending money to friends and a very quick way to loose said friend. 9 times out of 10.
I agree with what most have said above. Lending money that you expect to get back to family or friends is a horrible idea and I am very much against it. I would never do it, unless it was money that didn't care to have returned to me.
I will simply reitterate what others have stated. If lending money to friends or family ONLY give what you can afford to not receive back. If you can't do that don't lend anything and just say you're financially unable to do so. Money is not worth ending a friendship or being astranged from family over. Just is not worth it. Help when and how you are able don't feel like you absolutely have to either - if the person is a good friend or close family they'll understand if you are unable to help out.
You absolutely need something in writing, because when it comes to money, sometimes friends turn out to be less than trustworthy. However, once you have it in writing you have to keep in mind that you never loan anything that you could not part with. I have had to write off a loan for a friend because she fell on hard times (even harder times) after we agreed on the initial loan.
If he is a reliable person and you have faith in him then lend him some money, there are various banking facilities available that lets you to do this task.
most times when you lend money to freinds you will lose both your money and friend. Only do this with the expectation you will not get paid back.
If you do decide to lend the money, get it in writing so you have bad debt write off on taxes.
There are specific websites that allow you to design a loan and both parties have to agree. They may even facilitate the money transfer (not too sure about that). I know that these websites charge a fee, but it would be much better than having a written I.O.U in my opinion.
Yeah you lend to family and friends with the knowledge it will not be paid back. If it is, great! But go into it knowing they wont.
Take his car title as colleteral, have him sign it all over to you. If he has no car eesh =/