When Milo quits his job, Myron hires Jude, a pretty female writer, to replace him. Tyler tries to earn Jude's respect. Gibbs thinks his apartment is haunted while Neal has some apartment issues of his own. Milo struggles to prove himself as a real writer.

Jude warns Gibbs that dating a girl from the suburbs is more dangerous than it seems. Tyler and Milo's friendship is tested when Tyler offers to cover Milo’s share of the rent.

Tyler attempts to ask Jude out on a date, but her past gets in the way. Worried that Gibbs is bottling up his emotions, Milo tries to get him to cry. The big source of Neal’s sexual anxiety is revealed.

Tyler and Jude try to keep their new relationship a secret. Milo, already feeling left out since quitting Full Steam, has his traditional movie night taken away from him. Gibbs is hurt when Neal finds a new apartment. PJ tells a paranoid Myron to expect big changes in the office.