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You need a receipt as documentation that this was a loan being paid for, in case a government agency (like the IRS) ever comes knocking on your door. So, just tell them this. "Trust" shouldn'...

Since you specified "without implying distrust", I think it's at the heart of the matter, and consider it worth noting that the concepts of personal integrity ("my word is my honor"...

I think this one is pretty easy, and accomplishes the goals of not implying distrust and providing a record that you have paid the loan back. There are three options: Write a personal check in the ...

I've lent money to family. When I did so, after a couple months with no change in repayment (as they got back on their feet), I decided that it would be easier for me to say, "I'm never going to see ...

I had such friends. They'd ask me and my other friends for money. So, I am writing what I did. To avoid lending him money, you might wanna discuss about this. First of all, do not overreact when ...

He seems friendly [...] but when he takes a loan, he just plays hide and seek to them. This looks like someone only motivated by money and interested in getting money. As you said, you got a hard ...

There's a track record. Use that. I had this problem with a relative once, and I said something like this: Last time you borrowed money from me it took way longer than we agreed for you to pay it ...

Make a wire transfer of the money. Then you'll have documentation of the payment. If that is not possible, send a confirmation e-mail to the guy "I just paid you XX dollars, thank you for lending me ...

In a comment you said We do have a written contract, amended verbally to allow a lump payment. Which also introduces confusion to the mix. So simply take the contract, write on it or on a ...

I like @baldPrussian's approach and would definitely try that first. But if he won't let you repay the money with money, then repay the gift with a gift. Come up with something he would enjoy. ...

You make agreements when on good terms before things can go bad. You prefer a confirmation of your payment, so that no misconceptions can arrise in the future. This way, both of you have something to ...