When a driven young "top floor" Brody falls for the down-to-earth "ground floor" Jenny, it brings together two very different groups of friends – and raises the ire of one very disapproving boss.

Despite Mansfield's warnings, Brody tries to turn his fling with Jenny into something more by going on a date, but to his surprise, Jenny wants to keep things casual. Meanwhile, the downstairs gang gets fast and furious in a chair race gone wrong when they destroy Mansfield's irreplaceable office chair.

When a new office opens up on the top floor, Brody will do what it takes to beat out Threepeat to get it. Jenny doesn't like this competitive streak in Brody, who then gives the downstairs crew something worth fighting over to prove everybody gets competitive. Meanwhile, Harvard is thrilled to have a new female admirer… until he discovers it's overprotective Mansfield's daughter. Now he has to end it before Mansfield finds out.

Brody tries to buy the perfect gift for Jenny, but as Mansfield says, "What do you get for the girl who has nothing?" Brody's extravagant gift turns the downstairs gang against him and makes Jenny feel uncomfortable instead of flattered. Threepeat over-extends himself to buy matching jet skis and is now desperate for a bonus he's not sure he's going to get.

When Jenny and Mansfield each invite Brody to the same baseball game, Brody has to make a choice. Sit in the nosebleeds with his girlfriend or in the luxury box with his mentor. He ends up making neither happy and has to put things right with a gesture that has the whole stadium watching. Meanwhile Threepeat jockeys for position with Mansfield, and Harvard ends up out of his element in the wonderland that is the company luxury suite.

Tired of watching Harvard, Derrick and Tori blow their money on lottery tickets, Jenny convinces them to invest with Brody. One white lie later, they're all convinced they're rich and would be millionaires and Harvard decides to give Mansfield a piece of his mind. Meanwhile Brody and Threepeat have to give bad news to some of the firm's temperamental clients, including a fiery John McEnroe.

When Brody's hyper-competitive ex-girlfriend from business school, Heather, comes back into the picture, Jenny's worried that Heather's a better match for Brody. When they all take the stage for karaoke, the sparks begin to fly. Meanwhile, Mansfield realizes that his office has become a boys' club and decides to get in touch with his feminine side.

When Mansfield's assistant calls in sick, Jenny steps up to fill in. But when Mansfield turns out to be hiding the fact he's sick too, Jenny has to treat the world's worst patient, while Brody steps up to take the biggest meeting of his life without Mansfield by his side. Meanwhile downstairs Harvard is left in charge, but the power goes to his head when he goes toe-to-toe with Threepeat and the upstairs crowd who are demanding new phones.

When Jenny cashes in eight years of credit card points for a trip to Paris without Brody, he's left wondering where he stands. The time has come for him to tell her exactly how he feels about her...if Harvard will get out of his way long enough to do it. After lying on his resume, Threepeat has to learn fluent Mandarin in one day or face Mansfield's wrath. Meanwhile, Mansfield makes an announcement that could change everything.

Brody faces a difficult choice between the job he always wanted with Mansfield and the love he never expected with Jenny. So he tries to come up with a third option. Threepeat is forced to stay with Harvard after losing his apartment, but he soon discovers Harvard's place in a converted funeral home isn't technically zoned for the living.