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The pilot starts off with Megan in New York City video chatting with her friend Charlie from back at home while dying her hair red when suddenly her apartment burns down! In case her life couldn't get any worse, the next day at her job, her boss fires her but recommends her a new job in Palm Beach. She's flown on a private jet where she meet Laurel who offers her $1500 / week to tutor her granddaughters, Rose and Sage. If she gets them into Duke she gets all her student loans paid off!
Now in Palm Beach, she goes to visit Charlie and tell him she's back in Florida! Don't tell her dad or sister though! Megan returns back to the mansion to see the girls exercising and tries to get them to read their assignment. Seems this job is gonna be tough! Then Megan meets the very cute neighbor, Will, and they two head off to an art gallery where Megan learns Will isn't just another trust fund baby... he wants to be a sports photographer!
Megan is called for an emergency by the girls! She has to go to the photoshoot to sign as their guardian as the girls are under 18. But since Megan can clearly see Rose doesn't want to pose in a bikini, she refuses to much to Sage's shagrin. After, Rose goes to hang out with Charlie and when she finally comes home, Luarel is waiting with Sage and they fire her! She wasn't available when Sage needed tutoring (she was with Charlie, remember?) Luckily, Megan stands up to Sage and puts her in her place.
The next morning as Megan is ready to leave and after a quick chat with Rose who thanks her, Luarel summons her into her office. Not only does she still ahve her job, she has a guaranteed 6 month contract!
Megan goes to the Ball with Laurel to help chaperon Sage and Rose. However, there's one person Megan didn't expect to see at the party... her sister! taking Megan around to introduce her... Rose is very eager to meet Lily, but Megan seems less than excited and heads straight to the bar for some whiskey. She sees Sage being embarassed about the photoshoot in front of some friends and comes over to remind Sage about some photoshoot that doesn't even exist. Megan then disappears into a room for some alone time when Sage follows her in to tell her she doesn't need her help and that she invited Lily!! OMG! The episode ends with Luarel ...oh this show is gonna be soooo good!