A first-generation college student who graduated at the top of her class from Howard University, twenty-five year-old Mahogany Rose is an ambitious, intelligent, funny, beautiful black woman who prides herself on being the best and excelling at everything - except love. Over the years, her moderate self-esteem and high - although not unrealistic - standards have been consistently crippled by the hyper-sexual, superficial, ethically challenged millennial dating culture. She has just about accepted defeat. When the story starts, Mahogany, who's been suffering through a months-long sexual frustration, is on yet another disastrous date. Things go from bad to worse and by the night's end, she draws the conclusion that 'hoes are winning' and contemplates becoming one. Though her love life is a 'complete shit show,' Mahogany still holds committed relationships in high regard and finds hope in her roommate and best friend Shyra - a rare product of a two-parent household raised on a steady diet of romantic comedies, Catholic school, and Good Housekeeping - who's long-term relationship with Rodney is picture-perfect - or so it seems. Guided by a strong moral code, Mahogany has always managed to walk a straight and narrow line, despite habitual ridicule and questionable advice from her close friends Misha and Reign. But when Rodney's side chick surfaces and Shyra is left devastated, Mahogany loses all hope and the scale is finally tipped. To Misha and Reign's delight, Mahogany finally joins the dark side. Ironically, now that Mahogany has abandoned her high standards and expectations for love in favor of spontaneous, casual sex, she finally found the perfect guy, Kaleb. The sex is hot, the chemistry is crazy, and the emotions are so high that a one-night stand quickly turns into an ideal 'situationship' - except for the fact that Kaleb has a girlfriend. But by the time she finds out, Mahogany is in too deep. High on lust and drowning in ecstasy, the line between right and wrong becomes so blurry that Mahogany can barely recognize herself - let alone the hypocrisy of her position as the girl on the side.