Legal Question in Credit and Debt Law in Massachusetts

I loaned $500.00 to a guy 3 weeks ago in order to help him cover his rent since losing his job 2 months ago that I have since broken up with because of suspicious behavior with an ex-girlfriend. I wrote up two hand-written agreements we both signed and kept a copy of:

"I, (name) of (address, city, state), hereby loan $500 cash to(his name) of (address) to be paid back in full by December 1, 2009."

He told me he would prefer to pay me back in one lump sum and would be putting money aside every week. I have a voicemail from him from yesterday saying "I knew I should have never borrowed that money from you - I will do my best."

Will the agreement and/or the voicemail hold any water in court if it comes to that? A friend of mine said he is more in jeopardy and it is up to him to provide proof he paid me back (if he does) instead of just give me cash or I can claim that he never paid me. I have also drafted the following email to him. If he responds and acknowledges that he owes me $500 and that I want it back by check, will this hold any water in court?:

"(Personal comments about what occurred....)

Also, not sure why you said you knew you shouldn't have borrowed the money from me. Why is that? When I asked you a few months ago if you had people you could borrow money from, you said you did but you weren't going to. I wonder why you chose to ask me over the others in the end. As I mentioned earlier, I want the money back ASAP and would prefer it via check mailed to me:

(my name + address)

Please only respond to this email.... I can't handle talking to you right now.

(OR I COULD SAY....)

Please respond to this email that you understand and agree to the terms to pay me back.

(my name)

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