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The series follows Whitney Cummings, as she portrays a fictionalized version of herself, and her very supportive live-in boyfriend, Alex. Even though the two have decided that they will not commit to marriage, she does question how committed they are in their 3-year relationship and tries to go as far to prove a point. She begins to fear what she sees as "relationship boredom" and worries what will happen next that could possibly end their relationship. Because of what she sees and hears around her involving other relationships, she uses unconventional methods to keep the romantic flames glowing with Alex, often seeking the help of her close friends. The sitcom is set in Chicago