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if it isn't also your business, you made non-deductible gifts to your father-in-law. why didn't you get reimbursed by him? if over $15,000, and there is no intention for you to get reimbursed, you are supposed to file a gift tax return.
No. but the person you paid it for may be able to deduct it. The general rule is that a taxpayer must actually make the payment (as well as be legally liable to pay it) to get the deduction. However, there are court cases that seems to say that he can take the deduction even if you were they one that actually paid it under the theory that your paying the expense is just a gift to him, and it was therefore really his money that paid it.
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