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In order to escape her looming post-graduation fate that includes student debt and zero romantic prospects, Blake Conway becomes a sugar baby. As the aspiring journalist and hopeless romantic documents the adventure, she sets out on a quest to figure out if society is right to judge these women and if her own self worth comes with a price.
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.