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Sophie and Oleg welcome their baby daughter Barbara to the world. Randy returns to briefly continue his relationship with Max, but it does not work out. Randy wants Max to move to California, but Max, publicly acknowledging her strong friendship with Caroline for the first time, says she cannot do so because she has important people in her life now. Meanwhile, Caroline meets Bobby, a contractor who rebuilds the dessert bar after a storm, and the two start a relationship. By the end of the season, the movie about Caroline's life has been made (albeit with some "creative license" changes), but Caroline destroys a $10,000 on-loan dress at the premiere, which wipes out both her and Max's combined savings and returns them to "broke" status. Randy comes back to New York, this time permanently, and proposes to Max, who accepts
