Neal is going to propose to Amy, but first he has to get her father's blessing - and it's not going to be easy. Milo joins Gibbs on his yearly "samurai cleanse". Tyler finds his first gray hair and is convinced that the end is close? or at least closer.

Gibbs helps Neal plan the perfect proposal. When Neal doesn't get the answer he expected from Amy, Milo thinks it's all his fault. The guys accuse Tyler of "straight baiting" his new friend, who happens to be one of the richest men in America.

Myron, the new boss at Full Steam, has promised to fire one employee by the end of the day. When Neal shows up to work drunk, the guys rally to sober him up and save his job.

Milo's jealousy is tested when he dates a girl who has a "same-sex ex". Gibbs gets carried away with a "fake" marriage. Tyler tries to win Myron over with Neal's help.

Milo meets a book publisher (guest star Jane Seymour), but it's not his writing she's interested in. Neal hires an intern (guest star Ed Asner) and Myron enlists Tyler and Gibbs to make him look cool on social media.

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.

The guys follow a girl to a party to help Neal make a connection, but they get more than they bargained for when they learn that Molly isn't the host of the party - it's what's in the punch.

Jude warns Gibbs that dating a girl (guest star Molly Sims) 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.