The dating life in New York City can grow tiresome and wearing. Two good friends with opposite relationship problems found themselves single at the same time. Tim is afraid of commitment, often dating many girls at once, and he’s losing sight of what a healthy relationship means. Jessica is a hopeless romantic, jumping into relationships too quickly, always looking to find “the one.”Follow the story day-by-day, at fortydaysofdating.com See their dating rules video below