Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.
On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.