The story of a struggling scriptwriter who takes in a plucky Jack Russell terrier in hopes of charming its pretty owner into the bedroom. Lately, Bobby hasn't had much luck in relationships. An aimless New Yorker whose best friend Scott is an unrepentant womanizer and whose nemesis Hart Carlton steals his ideas for a corny morality play about 9/11, Bobby just wants to find a pretty girl and move beyond the petty disappointments in life. When the girl Bobby currently has eyes for asks him to take care of her Jack Russell puppy for a few days, the lovelorn lothario sees the good deed as the perfect opportunity to make an unforgettable first impression.