The agency is about to lose their largest client unless they can come up with a new fresh advertisement. Simon gets Kelly Clarkson to sing the promotional song.

Sydney creates a campaign for the Windy City Coffee Shop. While it is initially spectacular, when the wind blows, coffee is blown everywhere. Meanwhile, Zach & Andrew compete to find out who Simon likes more.

Simon tries to make up for Sydney's childhood memories by reteaching her to drive; Lauren enlightens Andrew and Zach on their relationship.

Sydney has plane tickets to Hawaii for vacation, but finds ways to delay leaving. The team tries to work on an ad for a breakfast burrito, but end up talking about everything else.

A new client, sophisticated and classy, has Simon, Zach, and Sydney falling all over themselves to be liked the best. Helena likes them all and it causes jealousy with the three.

The agency promotes an advertisement for men with functioning problems. So when Simon is nominated for an advertising award next to a younger man from another agency, Simon starts to feel his age.

Simon, Zach, and Andrew pitch ideas for Australia tourism, but Simon has a difficult time coming up with ideas. Sydney's former co-worker writes a song about her that she does not like. Simon uses the song for the Australia ad.

Simon is intent to make things right when his partner, Gordon Lewis, forces him to give up his very first client when it conflicts with another account.

Someone's job is on the line at the annual Accounts vs. Creatives 16-inch softball game, and the truth about Simon's last epic win threatens to surface.

Sydney's insecurities about how she is perceived resurface when the bratty daughter of an important client becomes their intern.

When Simon mixes up the assignments in the office, he puts Sydney on an account for a video game that she becomes addicted to winning.

Most of the team gets the flu and cannot work on any recent ads. Lauren has to take charge with a high-profile client, and it is her big break.

The agency hires a data analyst against Simon's wishes. They have a new client who sells cat food, and the data analyst has a better marketing idea than Simon. Sydney bonds with the cat, while Zach and Andrew try to cheer up Simon.

A woman asks Simon to eulogize her deceased father, a jingle writer who was not a well-liked man.

To help land an account, Zach is forced to be a DJ at a Bar Mitzvah. The child wants a Chicago theme, and Simon helps plan skits and images for the city of Chicago. However, the child wanted the musical Chicago.

Simon's desperation for grandchildren forces him to interfere with Sydney's new relationship. Meanwhile, Zach and Andrew try working with other partners.

Everyone makes plans to celebrate St Patrick's Day, and Andrew's sister visits to join the festivity. Except, Simon does not like the holiday and tries to pretend it does not bother him to hear all the plans.

Trying to channel Simon, Zach overpromises on a pitch and must get Brad Paisley to sing a jingle written by Danny Chase.

Simon's promising new relationship is tested when he becomes disillusioned with love after Gordon and his partner break up.

Simon and the team decide to use a new idea to save a library from being shut down while Gordon finds himself becoming the poster boy for the campaign.

When a corporation wants to buy out Lewis, Roberts+Roberts, Gordon calls in the board to vote, and Simon's ex-wife and Sydney's mom has the final say.