Simon loses a creativity contest to a research analyst, so Zach and Andrew try to help him refocus and get his confidence back. Elsewhere, Sydney bonds with a cat, causing her to worry if this will stifle her future relationships with fellow humans.
Sydney's enamored ex-coworker writes a song about her, and it has an alarming stalker vibe to it. Meanwhile, Simon has difficulty coming up with a pitch to promote Australian tourism because that locale brings back memories of his last drinking spree.
Simon wants to replace Sydney's bad child memories with positive new ones, so he teaches her how to drive again. Elsewhere, Lauren's comments about Andrew's behavior toward Zach crush Andrew's confidence.
Simon tries to persuade Kelly Clarkson to sing a jingle for his firm's biggest client in the series premiere of this comedy about an eccentric advertising exec who works alongside his levelheaded daughter at their ad firm.