Collin along with some of the other executives takes part in a game, a game in which they must date a woman who is basically ‘shy, homely and undesirable’. Collin has won this game every year and this year will be no exception that is until he meets Regina TalbotRegina 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 that of handsome Collin Noonan.Watch as Collin and Regina began on a road of self-discovery of themselves as well as the obstacles that will eventually causes problems for their future.