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Louise Harrington (Linney), a thirty-nine-year-old divorcee, works in the admissions office at Columbia University School of the Arts in New York City. It gives her pause when she receives an application from F. Scott Feinstadt, the same name as her high school sweetheart who died in a car accident, and she contacts the student to set up an interview. His physical appearance, mannerisms, and painting style are strikingly similar to those of her former lover, and she begins to think that the young artist may be the reincarnation of her former romance, which she dismisses. The two begin an affair just a few hours after meeting. Louise's life is further complicated by her relationship with her ex-husband Peter, who admits he is learning to cope with a sex addiction that, unbeknownst to her, plagued their marriage; her ne'er-do-well brother Sammy, who is favored by their mother Ellie despite his shortcomings; and her best friend Missy, who stole the original Scott from Louise before his death and appears intent on doing the same with the contemporary version.