Sending someone to court?

My friend talked to this guy for about a month and he offered to buy everything when they went out on dates. New Years Eve he bought a hotel room for him, her and her friends so they can Uber to NYE parties.

A couple days later she ended it with him and now he's harassing her, saying she's cold hearted and now she apparently owes him money. He wants to send her to court for "owing" him money but she never signed anything saying she has to pay him back.

He's the one who offered to pay, is it possible for him to win this case when there's no proof that said anything about her owing/paying him back all of a sudden?