Privileged - Season 1 - Eps 10: All About Overcompensating
Megan becomes more uncertain about where she stands in her growing romance with Will when he claims to have dated a lot more that she has, So, Megan asks Charlie's latest girlfriend, Mandy, to set her up on a blind date with one of her co-workers. Meanwhile, Rose gets a 'D' on her English exam and plots to keep herself from failing her upcoming history exam by stealing a copy of the test, and Sage devises a crafty plan so Rose will not get caught. Elsewhere, Laurel confides in Megan about her long-lost romance with her one-time boss, while Megan also learns that Lily is now dating her irresponsible punk boyfriend again.
About Privileged

Title: Privileged
First Air Date: 2008-09-09
Last Air Date: 2009-02-24
Status: Ended
Rating: 7.45/10 (from 20 votes)
Language: EN
Seasons: 1
Total Episodes: 18
Network: The CW
Genres: Drama
Production Companies: Alloy Entertainment, Warner Bros. Television, CBS Studios
Synopsis
Megan Smith, a smart and quirky young assistant at a glossy magazine, is fired when her Yale education proves detrimental to getting ahead in the world of tabloid journalism. Her boss takes pity on her and arranges an interview with the wealthy Laurel Limoges to be a live-in tutor for her twin teen granddaughters. The beautiful and rebellious twins are less-than-thrilled with their new tutor, but Megan is determined to win them over as she enjoys the perks of her new job - breathtaking private suite, gorgeous car and live-in chef.
Cast

Michael Cassidy
Charlie Hogan

JoAnna Garcia Swisher
Megan Smith

Brian Hallisay
William Davis

Lucy Hale
Rose Baker

Ashley Newbrough
Sage Baker

Kristina Apgar
Lily Smith

Allan Louis
Marco Giordani

Anne Archer
Laurel Limoges