Megan is concerned that Rose and Sage don't have enough extra-curricular activities to get into Duke, so she arranges for them to volunteer with a charity that provides prom dresses to under-privileged girls. Rose and Sage make a mess of the dresses they are supposed to alter, but they fix the problem in their own unique style. Meanwhile, Megan decides the time has come to reconnect with her estranged father and invites him to dinner at the estate. Megan asks Marco to prepare dinner for two, but when Lily, Will, Rose and Sage also show up for dinner, the party goes surprisingly well until Sage catches Lily in an embarrassing situation. Megan comes to a new understanding with her dad, but later that night, she has a nasty confrontation with her best friend Charlie.

Megan becomes more neurotic and uncomfortable when her eccentric and estranged mother Shelby, whom she hasn't seen in 16 years, suddenly shows up to visit Arthur. Megan instead confides in Charlie about her problems, which makes Will feel left out and a little jealous over Megan's friendliness with Charlie. Megan also learns that Lily has eloped with her punk boyfriend, which makes Megan feel that she's losing control even more. Meanwhile, Rose asks Marco to help set up Sage with the sous chief Louis, while Sage makes a bet with Rami the doorman to try to set up Rose with her old boyfriend Zack.

Rose tells Sage the truth about who their grandfather is, causing a confrontation between Laurel and the twins. Laurel gets more bad luck when Elyse Valencour, Miles Franklin's daughter, brings a lawsuit against her for emotional distress against her father when she informs her that Miles has been hospitalized from a fatal heart attack. Sage also confides in Rose that she feels indirectly responsible for their parents death years earlier. Meanwhile, Will's father decides to start a new magazine and Megan wants to contribute to the first issue. But Megan and Will soon meet the editor-in-chief, David Besser, whom is much harder to please than anticipated. However, the strain on both Will and Megan for the same job puts a strain on their relationship. Elsewhere, Marco goes to drastic measures to win Keith back when he finds him living with his best friend Jennifer who wants to get romantically together with Keith to start a family.