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 (guest star Kwanten). Nick's romantic plans are foiled when he finds himself spending more time with Julia's (guest star Caplan) law firm assistant (guest star Duke) than with her. Winston becomes one of the girls when Shelby (guest star Hawk) invites him over on the holiday.