Caleb desperately needs a new fake girlfriend. Either he attends a series of parties for his father's law firm with a pretty girl on his arm, 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, recently fired waitress and aspiring painter, is open to new experiences. It's the perfect setup for them both. Caleb has only one rule for the arrangement: Didi must not fall in love with him. The summer nights tick by in a whirl of lavish parties, and Didi is enjoying her foray into high society. But Caleb soon starts to worry that this time he's the one in danger of falling in love.