Collin Noonan has the world in his hands, being the youngest top executive at his firm, the envy of all men as well as the lover of many women. Collin, along with some of the other executives takes part in a game. A game in which they must date a woman who is 'shy, homely and undesirable'. Collin has won this game every year and this year, will be no exception that is until he meets Regina Talbot. Regina Talbot is your average 'Plain Jane'. She's never been part of the 'in crowd' always keeping to herself and is extremely painfully shy towards men. She never would think that any man would be interested in her, especially, as handsome as Collin Noonan. Watch as Collin and Regina begin a road of self-discovery of themselves as well as the obstacles that will eventually cause problems for their future.