Ashley (Lindsay Lohan) is the luckiest girl in Manhattan, great job, great friends, great life! But when she exchanges an impulsive kiss with accident prone cluts Jake (Chris Pine), they both find their fortunes turned around 180 degrees. As Ashley's life begins to slide out of control and into disaster, Jake's star is on the rise, while at the same time he is trying to win Ashley's heart in this sweet but unsurprising teen rom-com.
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