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.

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.

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.