Sydney is now living with Owen, feeling bad since she cost him his catering job. All good intentions aside, this mean she is constantly on first-date behavior: not using the bathroom in front of him, pretending to eat salad, only burping in elevators etc. Simon, who is desperate for grandchildren, hires Owen, meaning Sydney has to keep up her ruse 24/7. As it turns out, Owen is afraid of babies, so Simon calls out the deal breaker, instead of Sydney (which we see she's done many times). He tries to submerge Owen in a group of babies dressed in a client's cute outfits to get him accustomed to them. While Zach was on vacation, Andrew was paired with George, another copywriter, and needs to come clean to Zach about his "cheating." They have a "break up conversation" and act as hurt as if they used to be dating. Zach decides to try working with a slew of other people. Andrew goes back to George, but the rose tinted glasses are gone, and George's compliments begin to irk Andrew. He and Zach make up dramatically in front of a client during Andrew's pitch with George, "Don't get on that plane...account."