In "All About What You Really, Really Want," we start off with Megan ignoring phone calls from her sister Lily and Rose and Sage getting ready for their first day at school their very social week including Parker's yacht party.  Will comes over for breakfast and Megan is very cold towards him.  When he leaves she tells Marco she's not dating anyone right now.  When the girls arrive at school, the very cute headmaster, Jacob Cassidy, calls Rose into his office.  Due to her low grades, Rose is going to be held back a year!  Charlie and Megan head to the beach where Charlie and surfs and Megan tries to write but can't with her writers' block.  She tells Charlie about her Will / Lily problem and again Charlie seems shocked she'd like Will cause he's not her type.  We know, you are though Charlie.  Megan gets a frantic phone call from Rose about her problem.

When Megan gets home tells them she plans on trying to talk Rose's way into sophomore year as her tutor, though the girls think it doesn't matter because their grandmother can just buy their way into Duke like Parker's father bought him into Brown.  The next morning, Megan heads in to meet with Mr. Cassidy and runs into Will on her way out and again is very cold.  He tries to compliment her... she says it's inappropriate.  At the meeting Megan manages to talk Rose's way into sophomore year... and a possible date!  Mr. Cassidy asks for her number and she gives him her "work number," which of course she admits is her cell phone.

Megan shares her good news with Marco, who reminds her she needs to think about her love life right now.  Her "job" with the girls isn't what matters.  When Megan tells the girls about the good news and Rose's new "regime," the girls don't want to the plan to start just yet... tomorrow is Parker's yacht party!  The next day at school, Rose seems very dedicated to start studying and skip the party until Parker shows up to school.  Parker and Max (now her boyfriend) pressue Rose into going.  The girls decide to skip the rest of school to go shopping.

Megan is about to write when she gets a call from Mr. Cassidy, the girls are playing hookie and she should go into see him.  Lily meanwhile meets with Charlie at the beach and when Charlie tells her she seems shocked that Megan even likes Will.  Megan arrives at Mr. Cassidy's office who pretty much uses this meeting as a chance to ask Megan out again.  When she says no, he moves on to the girls who are playing hookie.  Megan goes off to find the girls on the yacht and tell them they need to go home... too bad the yacht just left the dock and she's trapped!

On the boat, Megan goes to find Rose but sees her angry at Max for telling everyone she was held back... decides there'll be a better time to talk to her.  Will, who's at a high school party for some reason, finds Megan.  The two talk and Will tells Megan that Parker never actually got into Brown and that's why he's taking this "semester off."  Will also learns why Megan is so angry at him and the two decide to be just friends.

The next morning Megan tells the girls how Parket never got into Brown and they'll actually have to study.  Rose then tells Megan, away from Sage, that she really does want to try but sometimes it's tough to get away from Sage.  Megan isn't going to force her.  Charlie stops by to see how things are going with Lily and Megan isn't ready to talk about it yet.  We see rather than going out, Sage decides to stay back and help Rose study!  Megan then asks Mr. Cassidy out on a date.