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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.
Even the neighbors are fabulous in Palm Beach and Megan quickly catches the eye of Will (Brian Hallisay), the wealthy and attractive dilettante who lives on the estate next door and just happens to be dating Megan’s estranged sister, Lily (Kristina Apgar).
Completing this romantic quadrangle is Megan's best friend, Charlie (Michael Cassidy), who is secretly in love with her.
Meanwhile, Sage invites Lily out to a restaurant to dig up dirt on Megan and the two end up drinking together, something that infuriates Megan.
Finally, Megan is worried when she thinks that Jacob might be losing interest in her.
Megan's friend from college, Caryn, comes to visit and suggests that she writes an expose on life in Palm Beach, an idea which Megan rejects.
Will invites Megan and Caryn to a tennis match he has been hired to photograph, but Megan accidentally tells his boss about Will's family's wealth, something he had been keeping hidden at work.
Meanwhile, Charlie confesses to Marco that he is in love with Megan, and Megan is convinced by Rose to invite Lily to the pool party but when things start to go wrong when Rose's tennis bracelet gets stolen and Megan blames Lily. Megan's relationship issues with the opposite sex reach a new level when she realizes that Jacob is still interested in his ex-girlfriend and Charlie decides to put the brakes on their friendship.
However, the event turns sour when Megan gets into a heated argument with her sister Lily, Rose spots her ex-boyfriend with another girl, and Megan has to rescue both Rose and Sage after the two get caught driving without a license.