Struggling single mom Katie Jacoby has always dreamed of being an actress. When she was little, she spent hours in front of the mirror reciting lines she'd memorized from books and her favorite movies. She practiced a million different accents and knew exactly what she'd say on the day that she accepted her Academy Award for best actress. Somewhere along the way though, life happened and she soon found herself settling for a far more practical job as a waitress. She's never been rich, but she's always been able to make just enough to pay the bills for her and her daughter. However, a recent chain of events has left her in a desperate need for a lot of cash-and fast. Privileged playboy Jordan Knight is the youngest member of a family of insanely rich Boston socialites. For the majority of his teens and twenties, he's enjoyed living off of his family's wealth and traveling the world in search of a good time. However with his thirtieth birthday in sight and no signs of settling down, his parents have called him home to Boston to demand that he find a sense of direction for his life or else. Scared, he'll be resigned to working the family business or even worse, end up completely cut off from the finances, Jordan realizes he must work fast to prove to his parents that he has everything completely under control. Thus, after a chance encounter places Katie and Jordan in each other's paths, they soon find themselves coming up with a brilliant plan to resolve both of their problems. All they have to do is play house for one night. It couldn't get any easier than that, right?