Let's Make a Date has Chip chhose from Wayne (All The Characters from Austin Powers), Colin (Dunk Tank Loudmouth Unknowingly Suspended Above a Pool of Piranha Fish), or Ryan (Series of Kids Coming to see Department Store Sanata Colin with their Christmas Wish Lists). In Duet, Chip and Wayne sing to Nicole the Receptionist in the style of swing. In Bartender, Chip tends to Colin, who is mad about his haircut, and Ryan, who is in love with his shoes. Chip hosts Party Quirks. His guests are Wayne (Entire Night's Entertainment at a Hawaiian Hotel Luau), Colin (Salty Old Sea Dog who can See Amazing Sights in People's Bellybuttons), and Ryan (Series of Temperamental Actresses Screen Testing for a Nude Sceen with Chip). The four sing the Broke Up Irish Drinking Song.

Chip wins, so Wayne, Drew, Colin, and Ryan act out the World's Worst person to be leader of the world in a crisis.