Fired after causing his shoe company to lose hundreds of millions of dollars, Drew Baylor (Orlando Bloom) is on the verge of ending it all. But he gets a new lease on life when he returns to his family's small Kentucky hometown for his father's funeral. Along the way, he meets a quirky flight attendant (Kirsten Dunst) with whom he falls in love, easing the pain of his recent break-up with his girlfriend (Jessica Biel).