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, 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.
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.
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.
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.