A series of interrelated relationships will challenge everyone involved in them. Tommy (Edward Burns) has a short relationship with Maria (Rosario Dawson), a commitment phobic woman he met in a video store. Tommy also dates Annie (Heather Graham), a married real estate agent that he meets while looking for an apartment. Annie starts her relationship with Tommy in order to heal her feelings of hurt due to her recent discovery that her husband, Griffin (Stanley Tucci), is cheating on her. Griffin is dating Ashley (Brittany Murhpy), a much younger woman that he met in the park. Ashley, however quickly discovers that she can do much better when she meets Ben (David Krumholtz). Ben, a hotel doorman and aspiring musician, is still trying to recover from his divorce from Maria. How will these confusing and inter-connected relationships turn out, and who will find a happy ending to their story?