asked again, answered again: NEED MORE FACTS ABOUT AMT AND CIRCUMSTANCES and why you think a bill might work and what else you have tried, etc. The is actually a methodology for collecting, but need more facts
If it's a family member, no don't send a bill. Call them! Tell them by phone that you loaned them money and they agreed to pay back XYZ amount. If they avoid your phone calls, pay a visit to their house. Let them know that you love them, but expect to be repaid.
I agree with jada_lynn that it depends on the words you exchanged when the money was given to this family member. Surely you protected yourself (I hope) by having some terms by which the money would be repaid. Depending on the terms, has the family member honored their end of the agreement?
They received your money, so they have to pay it back. The first contact should be firm and forthright, referring to the agreement you originally made, and stating that you want the repayment to be made or start to be made, depending on the terms.
Keep notes on what they say. Don't get into a fight or debate. State your position clearly, and give them a chance to do the right thing. But document everything.
It all depends upon you. If you think that you are running out of money and in need of money then go for it but if relationships are more valuable to you then reconsider taking back your money.
Are you considering sending a bill after the fact to make up for not having a written agreement to repay prior to completing the transaction with this family member? If that's the case then yes, anything in writing is better than nothing. Better yet, or in addition to sending in paper form, send a cleverly worded email about the loan, agreement to pay, timeframe or something to which this person must somehow respond. Maybe "accidentally" declare the wrong amount (a little more than was loaned) so that the family member might reply to you with "but wait, you loaned me xxx, not xxxx". Then if there's ever a denial about the loan ever having been made you have an acknowledgment from them that the debt does indeed exist. And by all means, PLEASE give a written receipt for all monies repaid to you which includes the amount paid thus far and the amount still owed to you. You're a nice person to help out a family member in need. Just sometimes people are taken advantage of and mistreated for their kindness by those they least expected it from. Good Luck.
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Other people asked questions on various topics, and are still waiting for answer. Would be great if you can take a sec and answer them