Billionaire Scott Hollister's ambition is to become a senior partner at his law firm. His track record is good and he has seniority at the firm, but he doesn't have the appropriate corporate image. He needs a house, an attitude adjustment, and, most importantly, a wife.

He finds a woman interested in dating him—not just in dating his wallet—but the woman he is falling in love with is a waitress at a local diner, who has mistaken him for being a homeless man after he has a mishap while jogging in the park.
He pretends to be penniless while courting Caroline, all while fighting off the corporate sharks who are also vying for the senior partner position.

Caroline's life is a mess, she's working three jobs and needs to support her elderly grandmother. She has no time for dating, doesn't need a boyfriend, but just can't resist Scott's charms. When the restaurant she works at caters for the Christmas party held by Scott's law firm, passions explode as they discover who they are and what truly matters.