In the first-season finale, Marco and Keith prepare for their nuptials with the help of a wedding planner (Kathy Griffin). Elsewhere, Megan and Lily gently confront their father about his drinking; Sage is hurt when she hears Rose is skipping their annual spa vacation to go on a wilderness trip; Will and Megan have a fight and break up; and Luis shocks Sage when he reveals he's opposed to gay marriage.
Will's father starts a magazine based on Megan and Will's idea, but the pair finds the editor-in-chief difficult to please; Marco tries to win Keith back, but he learns that Keith has renewed his relationship with a longtime friend; Rose reveals to Sage that Miles is their real grandfather, and, along with Megan, they confront Laurel; and Sage confesses her own secret that affects her relationship with Rose dramatically. David Besser: Robert Buckley.
Charlie tells Megan he's going to school in California and plants a kiss on her after revealing his feelings for her. Later, Will confronts Charlie at his going-away party after learning what happened. Elsewhere, Rose uncovers a family secret; and Sage fears Luis will be disappointed to learn she's a virgin, until she discovers he's deeply religious.
Will encourages Megan to distance herself from her family's problems and introduces her to his parents. Meanwhile, Rose and Zachary encounter a bump in their relationship when he discovers a picture of her, Sage, and Pete Wentz hanging out at a nightclub.
Upon learning that Lily is in prison, Megan rushes to her aid and discovers the reasoning behind her sister's imprisonment. Nonetheless, Will offers to bail Lily out, but Arthur refuses the help as a means to teach his daughter a lesson. Meanwhile, Rose aids Sage in picking out an expensive gift for Luis, but his reaction is nothing like what the twins had anticipated.
Megan finally confronts her mother (Sharon Lawrence) about her hurt and anger over being abandoned; Rose comes up with the idea of hosting a charity dinner as a way to help Sage spend more time with Luis; Marco's boyfriend tells him he should leave his job and start his own café; Mandy isn't happy when she hears Charlie is going back to school; and Megan gets a call that Lily is in jail.
On the heels of reuniting with her father, Megan is visited by her estranged mother (Sharon Lawrence), who abandoned the family many years ago. Meanwhile, Will becomes jealous when Megan turns to Charlie instead of him for advice on family matters; and Sage, who denies her feelings for Luis, sets Rose up on date.
Laurel travels to see her old flame Miles (Michael Nouri) in Santa Barbara, and a few days later he surprises her with a visit. But Miles soon realizes work and family come first for Laurel. Elsewhere, new couple Megan and Will face their first obstacle when he announces he's accepted a six-month job in Brazil; Megan prevents Rose from cheating on her final; and Charlie reconsiders moving in with his girlfriend.
Megan and Will finally begin dating, but the relationship faces early challenges when Megan discovers that Will is dating other women at the same time. Meanwhile, Rose begins to go to extreme measures to maintain good grades after doing badly on an English exam.
Sage and Rose's publicist gets them gigs at the opening of a hot nightclub, where Rose sings and Sage plays the guitar.