# Analyzing Don Draper's 18 Mistresses in Mad Men A breakdown of the complex romantic entanglements defining the protagonist's destructive personal journey. - **Source:** [Screen Rant](https://screenrant.com) - **Published:** 2026-11-11 - **Topic:** [entertainment](https://brifing.si/c/entertainment) - **Original article:** - **On Brifing:** https://brifing.si/s/61a9ce70-64d9-4ac8-8e84-a1795a145b48 ## The Pattern of Infidelity Don Draper’s character arc in Mad Men is defined by his chronic infidelity across seven seasons. While married to Betty Hofstadt and later Megan Calvet, he maintained a series of eighteen distinct affairs. These relationships served as a recurring mechanism for his psychological escapism from his true identity as Dick Whitman. ## Midge Daniels and Escapism Midge, a bohemian artist, was the first mistress introduced in the pilot episode. She represented a sharp contrast to the corporate world of Madison Avenue, offering Don a temporary refuge. Their relationship eventually dissolved when Midge succumbed to heroin addiction, highlighting the destructive nature of the people Don surrounded himself with. ## Rachel Menken's Unique Impact Rachel Menken was a rare exception as a client who briefly challenged Don’s professional boundaries. Unlike his other flings, she saw through his facade, recognizing that his desire to run away to Los Angeles was merely an attempt to escape his own life. Her later death from leukemia marked a somber reality. ## Surreal Encounters with Joy During a trip to Los Angeles, Don encountered Joy, a wealthy nomad who aggressively pursued him. This affair was particularly surreal, as Joy’s father, Willie, introduced them and later intruded on their intimacy. This brief encounter underscored the bizarre and detached social circles Don drifted into when he abandoned his professional responsibilities. ## Bobbie Barrett's Strategic Advice Bobbie Barrett, the wife of a client, engaged in a volatile affair with Don that ended after she gossiped about his private life. Despite the drama, she provided crucial advice to Peggy Olson, suggesting that women should leverage their gender rather than mimicking men to succeed in the competitive advertising industry. ## The Baltimore Trip Hypocrisy During a business trip to Baltimore, Don had a one-night stand with a stewardess named Shelly. This event highlighted Don’s profound hypocrisy; he engaged in infidelity while simultaneously judging his colleague Sal Romano for his own private life. The trip ultimately led to Sal’s dismissal from the firm, showcasing Don's power. ## Suzanne Farrell and Vulnerability Suzanne Farrell, Sally’s teacher, was one of the few women who perceived the deep sadness hidden beneath Don’s exterior. Their affair ended abruptly when Betty discovered Don’s true identity as Dick Whitman. Suzanne’s genuine concern for Don’s well-being during their final interaction stood in stark contrast to his usual transactional romantic encounters. ## Transactional Spirals with Candace In season four, Don’s relationships became increasingly transactional, exemplified by his frequent hiring of a sex worker named Candace. This period marked a dark spiral in his life, where he even introduced Candace to Lane Pryce. These interactions demonstrated his growing detachment from traditional social norms and his deepening emotional isolation. ## The Consequences of Recklessness The sheer volume of Don Draper’s affairs illustrates his inability to find fulfillment through human connection. From the heartbreak caused to his secretary Allison to his drunken slip-ups with Alice and Doris, his behavior consistently sabotaged his stability. Ultimately, these eighteen relationships serve as a map of his internal moral decay. ## Sources covering this story - https://screenrant.com/mad-men-don-draper-mistresses-girlfriends-romances-every/ — --- _Summary written by Brifing from the original reporting. Copyright in the original article belongs to its publisher; read the full piece at the link above._