The only way to earn the respect back from his boss is to either fire his girlfriend or his best friend.

Determined to prove to Mansfield that there is no place too low to start his climb back up to the top, Brody is working on the ground floor in an effort to get noticed. Unfortunately, the only people who seem to notice are Harvard and Derrick, and as they are worried that the superefficient Brody will soon have them out of a job, they come up with a mellow way to slow Brody down. Jenny is thrilled to discover she went to high school with Lindsay, but less thrilled when Lindsay's memories of high school cast Jenny in a whole new light.

When Brody gets his first paycheck from working on the ground floor, he gets the shock of his life. In an effort to downsize, he gives up his apartment and crashes with Jenny. But when crashing starts to feel a lot like living together, Jenny freaks out. Normally, Brody would turn to Mansfield for advice, but his boss has made it clear that this time Brody is on his own. Harvard and Derrick bet they know how to stretch their modest ground floor pay further than Brody.

When a rival, Jasper McCabe, starts poaching Mansfield's top guys, Brody thinks Mansfield will finally give him his job back, but when Mansfield makes it clear that things can never be what they were, Brody has to make a big change. At Derrick's urging, Jenny has to break up with Harvard - even though they have never dated! - so he will finally move on and pursue other women ... like the clearly interested Lindsay. Meanwhile, Threepeat has a hard time accepting the fact that Mansfield's rival has tried to poach everyone but him.

Brody is excited for the first day of his new job with his new boss, Jasper McCabe. That is, he is excited until he gets his first assignment: Take down Mansfield. Brody now has to go up against the man he has admired for years, and possibly drive his hero out of business. Meanwhile, Lindsay helps Threepeat fill the Brody-shaped hole in Mansfield's life. Downstairs, Jenny and Derrick help a newly single Harvard get back out there and introduce him to the world of online dating.

Brody is back upstairs in his natural habitat, and it's just in time for Mansfield's annual basketball tournament! He and Threepeat are excited, but when Jenny, who always regretted losing her college basketball scholarship, decides that she has something to prove, she signs the ground floor up to play too. Now the tournament is upstairs vs. downstairs and boyfriend vs. girlfriend. Meanwhile, Derrick tricks Harvard and Lindsay into going on their first date and Harvard learns that dating is harder than he remembers.

When Brody discovers Jenny never wants to get married it's a blow. When she says she doesn't like musicals, it's just salt in the wound. But Brody thinks if he can change Jenny's mind about musicals, maybe one day she can change her mind about marriage. Mansfield gets out of planning his daughter's wedding by pawning his wife off on Threepeat (who is in full wedding planner mode), only to later feel he's missing out. Derrick convinces Harvard he's taking things too fast with Lindsay - too bad the convincing didn't happen before Harvard visited a tattoo parlor.

Brody panics when Jenny invites the cultured and sophisticated Mansfield over to their zero-bedroom half-bathroom palace for dinner to thank him for paying for college. Meanwhile, Harvard and Lindsay are the perfect couple who never, ever fight - that is, until all their pent-up tension explodes in the middle of Jenny's dinner party. Plus, when Threepeat gets his 15 minutes of fame as a financial correspondent, he freezes up until he gets a little on-camera help from former childstar Derrick.

Brody's ex-girlfriend Heather returns as a partner in the company and Brody thinks he's falling behind. As a birthday gift, Jenny decides to help Brody cross something off his life goal list to cheer him up. Mansfield has the perfect island wedding planned for his daughter ... until the island sinks. With Lindsay's help, his hunt for a new wedding destination sends the whole office to sin city - Las Vegas! Harvard feels out of place in Las Vegas until he finds the wonderful world of craps. Threepeat instantly reverts to being Heather's assistant until he snaps and finally stands up for himself. Things take a turn when Jenny finds an engaging package in Brody's suitcase.

Jenny finds an engagement ring in Brody's bag; Mansfield dislikes his future son-in-law.