Chris Aquilino

Panicked by suddenly leading a much larger team, Richard finds himself managing a number of small conflicts in his efforts to unite his new employees. Dinesh celebrates a new purchase that Gilfoyle looks to spoil. Jian-Yang goes to court. Gavin is met with pushback over his signature and what it says about him.

Encouraged by Jared to strike up a friendship with a like-minded CEO named Dana, Richard instead finds himself enamored with Dana's suave COO, who prompts him to question his loyalty to Gilfoyle. Facing limited housing options due to his impulse purchase, Dinesh searches for a new roommate.

Richard decides to help when Laurie gets in a jam, but his lack of emotional discipline threatens to backfire on Pied Piper. Gavin tries to make a deal with a stubborn partner while abroad. Dinesh relishes a rare win. Jared bonds with a surprising figure.

When Dave is up for a promotion at work, Calvin tries to help him negotiate a raise from his penny-pinching new boss, Gregory (guest star John Ross Bowie). Also, Tina struggles with whether to share some sensitive information with Gemma.

Westport is known for its Halloween tradition of leaving an anonymous note and goodies on a neighbors' doorstep - called a "Boo". Katie is absolutely giddy when the Ottos receive their first "Boo," only to find out it was put there by accident.