After leaving her long-time boyfriend, Jess moves into an apartment with three men, and tries to re-enter the dating world.

When Schmidt's plans for his 29th birthday fall apart, Jess takes charge and enlists the help of her school's party hungry vice-principal. Meanwhile, Nick begrudgingly has his first date at Schmidt's party with a beautiful lawyer who harbors a secret, and the gang wonders who placed a 50 dollar bill in the douchebag jar.

Reagan challenges Nick and Winston's indecisiveness when she says she will sleep with only one of them; while looking at wedding venues with Cece, Schmidt runs into his college frenemy, Benjamin.

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.