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.

Against Nick's wishes, Jess makes it her mission to get the loft's cantankerous landlord to like her. In doing so, she inadvertently jeopardizes their living situation and the guys are forced to admit they've made some "unofficial" changes to the apartment. Meanwhile Schmidt tries to decipher what he thinks are mixed signals from his boss Kim .