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Applying logic to your argument, always dangerous when considering tax law, I think it falls apart. Should you pass on the street a stranger who's pushing a pram and holding a cup out to passersby and decide to give her a $20, that's a gift. Your connection with the waitress remains the service she's providing.

Great post, as usual, but I'm going to be deliberately difficult/obtuse here. Let's say that I'm single and romantically interested in a young waitress at the local diner. Business is slow and in chatting I come to learn she's behind on her electric bill and it's going to be cut off. Is it a gift or a tip if: a.) I write a check to the electric company directly, b.) leave a tip and some extra cash for the express purpose of allowing her to pay the electric bill, or c.) write an amount for both the tip and electric bill on the tip line of my credit card slip. Does it make a difference if I'm a regular or if it's my first time there? There's a continuum between a strictly waitress/patron relationship and friendship that can occur--where's the line between tip and gift?

Continuing the food service and transfer of money in films basic theme, while veering slightly, let us consider It Could Happen to You. Gift? Tip? Partnership?

Regarding the It Could Happen to You reference, the basic premise actually happened in Yonkers, NY: It would be interesting to know how the tax situation was actually handled. From what I gather, the waitress was involved in choosing the numbers before the "investment" in the lottery ticket was made, so I think a case could be made for it being a partnership. On the other hand, the offer was made in lieu of a tip, so I'm thinking technically it would be considered a tip.
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