White Palace (1990)

Max Baron (James Spader) is a 27-year-old high-flying advertising executive still recovering from the death of his wife. One night he is in a bar when he meets Nora Baker (Susan Sarandon), a 43-year-old waitress with a fixation on Marilyn Monroe. The couple gradually fall in love, though age and social differences mean that the path of true love is strewn with problems.