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Loan snarked: How do you ask your parents to pay you back money?

Have you ever found yourself in a position to have the means to help our your parents and you loan them money? More importantly, did you and your mom and dad discuss if this is a loan or a good natured, give them money and don't expect it paid back?
The real dilemma is how the money was loaned, the circumstances surrounding it and if it was made clear what happens to the money.
Plenty of kids have the means to loan money, finding themselves with extra cash in a savings account for instance and wanting to be the good son or the stand up daughter and help out their parents, the people who put you up for the first 18 or so years of your life.
That mindset is admirable, but if you're about to loan money to your mom and dad for bills, medical expenses or if they're short on cash, you need to set a clear expectation for that you want in return, if anything.
This may, in fact, be a good natured gesture of simply handing over money and wanting nothing in return. Often times, parents might feel sheepish about borrowing from their kids and you get a "I'll pay you back" in return. Those words can be rather hollow as a son or daughter, particularly if you know your parents don't have the money and you don't expect they will any time soon.

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What you need to do is tell them you don't expect it back because of their situation, but if anything changes then that's fine, and they can make things right with you.
What tends to complicate the matter is if nothing is said when the money is passed from child to parent, and no one knows exactly what type of transaction this truly just was. You, as the child, are going to start resenting the fact that you loaned money, and you're not going to get it back. If that money was needed, you have to be open and honest with mom and dad and let them know this is a loan or else you can't toss aside all the money you have saved.
Whatever the circumstances, you have to be up front about any time money is given from one person to another. Not expecting it back is fine, but being the "nice guy" and trying to help out can't be in lieu of going against what you truly want: the money paid in full back to you.

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