Dear Dave,
The guy who has been my best friend since grade school recently asked me to loan him $5,000. All I have in savings in $5,000, but I would be willing to give him $1,000. The problem is that while heís a great friend with a good heart, heís always getting himself into binds when it comes to money. Do you think I should give him $1,000?

Dear Israel,
If I were in your shoes, and I was going to give this guy a fifth of everything I had, Iíd want to know it was going to save his life. From what youíve said, it sounds like heís just out of control with his money while youíre trying to save. That being the case, Iím not sure youíd really be helping him.
If you want to gift your friend some money, then do it. But thereís no way Iíd tell you to give him everything youíve managed to save. And I certainly wouldnít do it as a loan.
Ask yourself if you believe deep down in your heart that giving this guy $1,000 would truly be a blessing to him or if, by doing it, youíd be acting as an enabler and basically just funding more of his stupidity with money. From what youíve told me, I think thereís a good chance the answer is the latter. And if thatís the case, you can be a much better friend by saying you love him enough to not ruin your friendship.

Confirmation of payoff?

Dear Dave,
After struggling with it for several years, I finally made the last payment on my Sallie Mae student loans this week. Do you think I should ask for a formal letter stating that itís officially paid off?

Dear Angela,
Congratulations on finally kicking that old woman out of your house! It feels great, doesnít it?
Sure, it couldnít hurt anything to write and request formal confirmation that the book on your loans is closed and everything is paid in full. You can do this through email so youíll have a record of contact, or you can send a certified letter, return receipt requested, through the post office. That way, youíll have a record they signed for it.
Following up on paid-off debts is always a good idea, Angela. You donít want the hassle of possibly having to deal with greedy or incompetent collectors sniffing around three or four years down the road and no way to prove youíre free and clear!

Dave Ramsey is Americaís trusted voice on money and business, and CEO of Ramsey Solutions. He has authored five New York Times best-selling books. The Dave Ramsey Show is heard by more than 11 million listeners each week on more than 550 radio stations and digital outlets. Daveís latest project, EveryDollar, provides a free online budget tool. Follow Dave on Twitter at @DaveRamsey and on the web at