Katie and Greg dislike Taylor’s new boyfriend, so they attempt to use reverse psychology to drive a wedge between them, which later backfires. After Spencer’s over-the-top vision for Oliver’s first date with a girl from his ballet class bombs, Greg helps Oliver make up for it with a romantic gesture.
Katie is worried that the launch of Greg’s new book might go poorly, so she enlists Angela and Doris to write positive reviews; when the book unexpectedly does exceedingly well, Greg buys a new car without consulting Katie.
Taylor enlists Oliver to help her carry out a scheme so she can ditch her less cool friend Ellen and go to a concert with her “blondetourage.” Meanwhile, Katie is devastated when Anna-Kat doesn’t need her as much anymore, which causes Katie to make some poor and desperate parenting decisions.
The Ottos struggle to be together for Christmas; Taylor teaches Oliver how to ask out a crush.
Greg and Katie are ecstatic to meet a couple without children; Anna-Kat coerces Taylor and Oliver into helping her with a storytelling project.
Dani and the Boys
Danielle learns the ropes and uses her wits and charm to help Mike and Frank get the prices they need on items across the United States
The Mother Load
Mike and Frank accept an invitation from Indiana’s Model-A Ford lady and fall hard for her ultra-rare, barn-fresh Model-A tow truck.
Katie teams up with Oliver to bribe rich Westport families to donate big-ticket items for the spring gala; Greg takes Taylor and Anna-Kat to a Revolutionary War reenactment.