Caleb desperately needs a new fake girlfriend. Either he attends a series of parties with a pretty girl on his arm to schmooze for his father's law firm, or he gets shipped off to Yale to start a future he's not ready for and isn't sure he wants. And sadly the last unattached girl in his social circle has just made the grievous mistake of falling in love with him. Fortunately, Didi, the waitress at the Country Club - who just lost her job due to Caleb's too-public breakup - is open to new experiences (and art supplies are expensive!). It's the perfect setup for them both. Caleb has only one rule for the arrangement: Didi mustn't fall in love with him.