Jess takes advantage of her jobless status to mingle with men at Nick's bar, leading to shenanigans particularly when she assumes the identity of a man's online date named Katie. Meanwhile, Winston's family is in town and Schmidt tries to get with his sister.
Tropes:
- Abhorrent Admirer: After getting Jess' number, Bearclaw takes things too far by immediately telling Jess how much he loves her; she is constantly repulsed by him.
- Betty and Veronica: Andy is the Betty to Sam's Veronica for Jess.
- Coitus Interruptus: Jess and Sam go into the bar's men's room to have sex in one of the stalls, but are promptly walked in on by Andy and Bearclaw.
- Everyone Calls Him "Barkeep": "Bearclaw"'s real name is never mentioned.
- Friends with Benefits: At the end of the episode, Sam tells Jess he doesn't care that she lied about who she was, as he remains interested in a sexual relationship with her.
- Love Dodecahedron: The main plot of the episode focuses on Jess' simultaneous encounters with three men: Andy, a nice but boring guy who she initially notices, Sam, a handsome guy who she falls even harder for but who is looking for someone else, and Bearclaw, who is very attracted to her but whom she is repulsed by.
- Mama Bear: Winston's mother Charmaine hates Schmidt and strongly opposes his advances on Alisha.
- Romantic Wingman: Nick tries to help set Jess up with guys she's attracted to at the bar. However, he doesn't do a great job of it.
- Screw This, I'm Outta Here: Andy quickly ditches Jess once he learns of her involvement with Sam and Bearclaw.
