The love lives of several people of various ages intersect when a young woman named Chloe (Alexa Davalos) comes to town. Immediately, barista Oscar (Toby Hemingway) is enamored with her and thrilled when his boss, Bradley (Greg Kinnear), hires her. Then Bradley's wife, Kathryn (Selma Blair), leaves him for someone else. Afterward Bradley marries realtor Diana (Radha Mitchell), who helps the first couple move in together. Harry (Morgan Freeman) watches it all quietly and muses on love and loss.