When Mason wins a promotion within the advertising agency, he must leave behind his best friend Connor. This forces them to reexamine their relationship as both brotherly friends and colleagues in the fiercely competitive ad agency world.

It's Conner to the rescue when an important client shoots down an advertising pitch. As the new pitch settles in, trouble arises which may put Mason on the unemployment line. Sarah adds to the stress with a full-court press for her office and objections to Mason's choice of a partner for her.

Mason puts his job on the line when he promises the CEO that Sarah will bring his team amazing success. Unfortunately for Mason, he is unaware that Sarah is not only frustrated with her job but is also entertaining another firm's job offers.

Adding to the angst, Conner runs into an old flame, making him wonder what could have been.

Mason misses the mark when he surveys his atypical daughter about trends with typical teens. It's up to Conner to save the day when Mason keeps digging himself into deeper trouble with the client by making promises he may not be able to keep. When Sarah's romantic life is called into question, Hector and Tom compete for the opportunity to clear up the matter.

Production comes to a grinding halt when a client decides to rethink the campaign. Conner puts jobs on the line when he chooses to continue production with overconfidence in his ability to convince the client to move forward with the commercial.

To celebrate her birthday, Sarah tries to go back to the way things were when she attempts to reconcile with her ex-husband.

Already worried about losing his job, Tony receives some unexpected news about his daughter which sends him reeling.

Mason gets Tony to give the group a chance to work on creative for Chicago's Olympic bid; Mason spends a long weekend with Erin and leaves Conner in charge; Sarah gets a new partner.

Conner and Mason both find themselves in situations of financial hardship that convince them they need to search for employment elsewhere; Sarah encounters setbacks that lead to others competing to take over one of her accounts.

The Mink group is engaged in an intense bidding war to become the agency of choice for Hydrenaline, a new energy drink. But trouble brews after Mason finds out the brand manager is sleeping with one of his team members. When Sarah tries a dating service, Conner helps her articulate her criteria for a perfect match. And Erin, worried that Mason may have a wandering eye, pays her husband a surprise visit in his office.

Tony loses all control of his anger when Simon and his group jump into the competition for the beer account that Sarah worked so hard to bring to the company, which leaves her feeling torn between the two teams.

While Conner works on the bum assignment of making a birthday video for Tony, he unwittingly discovers an interesting office secret.

Mason receives an unfavorable evaluation at work, causing an angry outburst and Tony to hire a corporate therapist to help the group through a number of issues. Meanwhile, Sarah finds her new relationship blossoming and seeks the blessing of her ex-husband, only to discover the brutal truth of why he divorced her.

On the set of her Dove commercial shoot in Los Angeles, Sarah immediately clashes with the nightmare director and becomes irritated when Mason won’t stand up for her in front of the client. Determined to save his group, Tony tries to poach a neglected account from a rival group. He even decides to make Conner his partner in the endeavor, widening the gulf that has developed between Conner and Mason.

After the Mink group wins a huge account, Denise sees Mason as the true creative force behind the victory and offers him a big promotion. Conner gets some serious news about his affair with an energy-drink marketer. And Sarah frets over how to break up with her boyfriend.