After failing to get donations on her own terms, Katie gives in to the dark side and teams up with Oliver to bribe rich Westport families to donate big-ticket items for the spring gala. Greg decides to take Taylor and Anna-Kat to a Revolutionary War reenactment which Taylor finds lame until she starts a revolution of her own.

When Doris goes into labor and Katie heads to the hospital to be with her, the Ottos struggle to be in the same place at the same time in order to open their Christmas presents together, as is the Otto family tradition. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush, starting with the gift shop clerk.