Navigating your way through love can be just as complicated as trying to figure out New York city's subway system. Henry and Nicole are two heartbroken people who weren't looking for love, in fact they really gave up on the concept. But fate seems to have a different plan. The question is, what happened in their pasts that has discouraged them in finding true love. One year prior to their meeting, Henry is getting ready to graduate from law school when he meets his soon to be best friend and roommate, Jim, a fast-talking womanizer. Nicole is trying to figure out not only how to stay out of jail but also wondering what life in Wisconsin will be like after her sister Karen, drops the bomb of her choice to move to New York City.