When money paying back money owed to someone over $14,000?

They won't think its a gift as long as you have some documentation that she gave you the money earlier. A simple bank statement showing a deposit (from her) of 14,000 would prove that you're repaying her. Technically since its a loan you should also pay her interest, but at this amount its really not necessary. The interest "lost" would be considered a gift, but as long as the interest lost is less than 14,000 (the amount of annual gift exemption) you don't have to report it.

A loan is not income, so paying back what you borrowed is not taxable or a gift. The IRS is more concerned with people depositing or spending significant amounts of "cash" of undetermined origin, than something like a check which has a verifiable chain of who gave who what. So it is cash that appears from nowhere that sparks their interest more than someone depositing a check or electronic transfer from a known person, even if reporting is required for both if the amount is significant, whether 1 payment or a series of payments.

Since the limit is an annual limit, not a lifetime limit, the safest approach is to give her half now, and half in January. That way, it's only $10,000 in each year, so it's not over $14,000 in either year, and even if they think it's a gift, you wouldn't be taxed on it.

Just write her a check. No need or reason to file a gift tax return.

And btw, it would't be subject to gift tax anyway unless you've given away a couple million + in your life -sounds pretty unlikely.

If you are paying through a bank and they ask you you can tell them that you are paying back a family member. If you don't want to be that personal you can get it in cash and give it to her in person. :)

The lifetime exclusion for gifts is $5 million dollars. long run, this won't incur any gift tax.

pay half now and half January 1, assure there is a document that says it was a loan, interest rate, etc.

IRS probably doesn't know or won't know anything about it

Don't mention it to IRS unless you are asked.