There's two sides to every love story

Nate Shepherd, late 40's, and Jenny Sparks, early 30's, meet in a fancy New York eatery. Complete strangers who have had a rotten day, waiting for their better halves, they reveal to one another that they are going to meet new people tonight. They quickly realize they are waiting for each other. When Nate loses his girlfriend (after getting fired from his cushy job at an ad agency) and Jenny loses her boyfriend to a drug overdose, Nate's girlfriend suggests that they should move in together as friends to split the rent and ease each others pain. As their friendship grows into something more, their relationship becomes a loving but complicated experience.