Average guy Kirk can't believe his luck when, against all odds, Molly, a successful and outrageously gorgeous babe, falls for him. Kirk is stunned and so are his friends, his family, and even his ex-girlfriend. Now, he must go to great lengths to figure out how to make the relationship work and prove to himself, and everyone else that she is not out of his league.

A young ladies' man, David, teaches his dating tricks to his lonely, widowed grandfather, and plays his best mind games in order to meet the woman of his dreams. But as David's games begin to fail him, Grandpa quickly transforms into the Don Juan of his nursing home. Slowly the teacher becomes the student, and it's up to grandpa to teach David that the best way to win the game of love is not to play games at all.