Privileged Episode Rating Graph

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 seeks to aid her sister, and in so doing learns why Lily is in jail. Will offers to bail Lily out, but both Arthur and Megan refuse saying that Lily should learn a lesson by staying in jail for her long history of making the same dumb mistakes and getting involved with the wrong people. Shelby secretly meets with Will behind Megan's back to ask for his assistance, and he agrees to help... only to find out later what Shelby's real reason is. Meanwhile, Rose helps Sage pick out a lavish gift for Luis to further get his attention, but neither sister foresees his reaction, while at the same time, Rose finds a love poem and assumes that her nebish classmate Zack wrote it for her.

When Megan tells Will that her mother has disappeared again, along with his money, Will suggests that it's time for Megan to separate herself from her family's problems. However, Megan is heartsick that Arthur is in denial about the situation and Lily is angry and hurt that she didn't even get to see her mother. When a picture of Rose and Sage with bassist Pete Wentz of the band Fallout Boy at a nightclub upsets Rose's boyfriend Zach, Sage has to admit that her pursuit of fame is taking a big toll on their social lives. Meanwhile, Laurel gives Marco the money to start his own restaurant, but he realizes that isn't what he really wants. Finally, Megan meets Will's parents, Elliot and Josephine, and feels guilty for involving Will with her own dysfunctional family, but Will surprises Megan with a declaration of his true feelings for her.

When Charlie announces that he will be leaving down to go back to college in San Diego, Megan's natural neurotic reaction is that she fears she will never see her best friend again. Then one evening during planning for a going away party for Charlie that his girlfriend, Mandy, planning, Charlie kisses Megan and expresses that he loves her which fills her with conflicting emotions, and fills Will with anger and jealousy. Meanwhile, Sage tells Louis that she happens to be a virgin, and gets a surprise when he tells her the same about him, and in an attempt to understand her better, invites her to his church. Also, Rose confides in Zack that she is not a virgin, and he reveals the same about him... And a twist comes when Rose gets a visit from Elyse, the daughter of Miles Franklin where she confides the secret that Miles is her late mother's natural father.

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.

While Marco and Keith plan for their upcoming commitment wedding, Rose and Sage's sisterly relationship takes a bad turn when Rose decides to ditch their annual plans for spring break and go someplace on her own, in which Sage becomes upset. Zachary too feels that Rose is maturing rather quickly, and worries about the future of their relationship. Sage has relationship problems herself when Luis tells her that he does not believe in gay marriages and refuses to attend Marco and Keith's ceremony. Elsewhere, Will and Megan have a fight over their creative differences over Will's job and Megan's mental ability to be independent. Also, Megan finally finishes her biography about Laurel who approves it for publishing.