When a self-proclaimed Boston Celtics #1 fan tries for $300,000, he tries to also hit on a Boston Celtics cheerleader (one of the episode's "visiting class"). Jeff teases him about it.
Then when she tells Jeff "Of Course!" when he asks her if she'd let the Fan keep his Celtics stuff, Jeff turns around and tells the Fan, "Now That's a Woman right there!"
He'd earlier quipped to the Fan, "You're single, aren't you?" when the Fan admitted he had Boston Celtic underwear, and did a bit of old material where when he got married, his wife went to HIS stuff like a flight attendant bidding passengers off the plane: "Bye-bye...bye-bye... thanks for coming, bye-bye..."
Jeopardy! champion Ken Jennings is always funny, and this show is no exception. When he gets to the Million Dollar Question, Jeff remarks that the audience always chants "Do it!" and Ken snarks "Yeah, they're never like, 'Go home! Open an IRA!'" He also talks about how the giant dollar signs on the big screen are hypnotizing him into going for it.
A really dense contestant that already dug herself deep by making herself look extremely stupid openly tells Jeff "I hear what you are saying, but I am only hearing what I want to hear." Jeff snarks back with "That's because you're a woman. Women want to hear their own opinions with a deeper voice."