|Season One, Episode Two|
|Air date||October 3, 2013|
|Written by||David E. Kelley|
Sidney creates a campaign for the Windy City Coffee Shop. While it is initially spectacular, when the wind blows, coffee is blown everywhere. Meanwhile, Zach and Andrew compete to find out who Simon likes more.
- Robin Williams as Simon Roberts
- Sarah Michelle Gellar as Sidney Roberts
- James Wolk as Zach Cropper
- Amanda Setton as Lauren Slotsky
- Hamish Linklater as Andrew Keanelly
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