Jess accidentally walks in on Nick naked, sending his self-confidence to an all-time low - just after an attractive co-worker agrees to go out on a date with him. Meanwhile, Winston becomes obsessed with learning pop-culture references online.

Jess reluctantly dates the wealthy father of one of her students. Meanwhile, Nick attempts to buy a new cell phone and Schmidt and Winston get ultra-competitive playing bar trivia.

Jess and Nick examine their friendship. Elsewhere, Schmidt hopes to impress an attractive Republican by pretending to be one of Mitt Romney's sons.

Jess and Sam go on a weekend getaway with Nick and Angie. But this might not be the trip they expected when Jess starts to party and trouble begins. Could jealousy get in the way of a good time?

Jess and Nick, who are caught between friendship and something more, try to break out of relationship-limbo by going on a First Date. Once Schmidt and Winston realize a full-on Jess/Nick romance might be happening, they swoop in to try to sabotage the date.

Schmidt sets out to sabotage Jess and Nick's relationship.

At the last wedding of the summer, the gang makes a pact: Each of them will get lucky by night's end. Jess sets her sights on the best man, who also has caught the eye of a beautiful scientist. Meanwhile, Schmidt and Nick get an indecent proposal. Winston recovers from his police academy training, and Coach panics when he realizes he already has hooked up with every woman at the party.

Nervous about Ruth's interview at a prestigious pre-school, Schmidt recruits Jess to help her prepare. Meanwhile, Nick procrastinates writing, and Winston prepares to confront his fear of testifying in court.