In this Judge Judy, a 27-year-old man sues a 13-year-old girl for false arrest. (She alleges he pulled a gun on her). She and her friends would harass and threaten him into buying them booze.
This episode is from Judge Judy: Second to None, a DVD compilation of some of Judy's best cases. The man in the clip showed terrible judgment in the past, buying a bunch of 13-year-old girls booze upon request. JJ asked the girl if she gave the man money for the alcohol. She said no, so JJ asked her if she paid him in any other way. Again, she said no, but JJ didn't really believe it, because there was obviously something weird going on that grown man had befriended 13-year-old girls who liked to drink. In the end, JJ didn't award him any of the damages he was seeking from his false arrest claim, since he'd already contributed to the delinquency of minors by buying the girls alcohol on numerous occasions.