Some Girl (2013)

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A man, who is only identified as "Man," is on the verge of getting married. He decides to revisit some of his former girlfriends due to having a guilty conscience for having treated them poorly in the past. His journey includes visiting his high school sweetheart, his best friend's little sister, a sexually liberal woman, a married college professor, and a woman he could have married in Los Angeles. Adapted from a stage play, the movie takes its audience through the rough waters of messy breakups from the perspective of a man who has second thoughts about having behaved badly. The reunions take place in upscale hotel rooms in cities spanning the country from Boston to Seattle.