Single for the first time on Valentine's Day, Jess convinces Schmidt to be her wingman as she attempts to have an attachment-free fling with a handsome stranger. Nick's romantic plans are foiled when he finds himself spending more time with Julia's law firm assistant than with her. Winston becomes one of the girls when Shelby invites him over on the holiday.

When Nick is hurt playing a game of touch football and Jess discovers he doesn't have insurance, she brings him to her doctor friend - an OB-GYN. The gang rallies together and Nick evaluates his life when his seemingly innocuous back injury may prove to be more serious than thought.