Don Draper (Jon Hamm) had 19 mistresses throughout Mad Men's seven seasons, not counting his three wives, making all of Don Draper's mistresses difficult to keep up with. Mad Men was one of AMC's prestige series that followed the lives and careers of Madison Avenue advertising executives throughout the 1960s. While the other ad men of Sterling Cooper also carried on extra-marital affairs, Donald F. Draper had the most by far. While Draper is married to Betty Hofstadt (January Jones), the character went on to have an unrivaled infidelity streak.

Despite having two kids with Betty, Don cheated on her numerous times as his advertising career took off. In Mad Men season 3, Betty, who long suspected Don's infidelities, learned that he's really Dick Whitman. Betty divorced Don, who then married his secretary, Megan Calvet (Jessica Pare) between seasons 4 and 5. He couldn't stay faithful to Megan either, and despite attempts to keep his private life and work life separate, Don's affairs were well-known within Sterling Cooper, and it's obvious that Don had many more affairs beyond what was shown onscreen. Regardless of his offscreen affairs, there are 18 of Don Draper's mistresses in seven seasons of Mad Men.

18 Midge Daniels

Played By Rosemarie DeWitt

Midge (Rosemarie DeWitt) is the first of Don Draper's mistresses introduced in Mad Men's pilot. Midge is a bohemian artist who is a sharp contrast to the slick Madison Avenue an. It offers him a bit of escapism from the corporate world as Midge and her friends see it as the enemy of the people.

Midge is also a swerve as audiences are initially led to believe she is Don's significant other before the end of the first episode reveals Don has a wife, Betty, and two young children in the suburbs.

She reappears in Mad Men season 4 where she is married to someone else.

Don's fling with Midge ends in season 1 when he discovers that she is in love with one of her male friends, and she refuses to go on a trip with him. She reappears in Mad Men season 4 where she is married to someone else. Sadly, Midge has become addicted to heroin by that point and Don cuts her a check as if washing his hands of her before vanishing from her life.

17 Rachel Menken

Played By Maggie Siff

Don tended to avoid mixing his affairs with his professional life, but there was one notable exception. Rachel Menken (Maggie Siff) was a Sterling Cooper client who owned a department store. Don didn't pursue his mutual attraction to Rachel until after he ended his affair with Midge, but his fling with Rachel didn't last long. However, Don did confess details of his life as Dick Whitman to Rachel.

She was a big part of the Mad Men cast in season 1 and he even proposes that they run away together to Los Angeles. However, she realizes he is simply running away from his life and using her as an excuse. In Mad Men season 2, Don runs into Rachel, who is now married, and in season 3, Don is sad to learn that Rachel died of leukemia.

16 Joy

Played By Laura Ramsey

While some of Don's mistresses don't last long, they mostly all reveal something new about his character. Joy (Laura Ramsey) is a wealthy nomad Don meets when he travels to Los Angeles in the Mad Men season 2 episode, "The Jet Set."

Don abandons Pete Campbell (Vincent Kartheiser) and stays with Joy and her strange, aristocratic friends for a few days before he leaves to visit Anna Draper and then return to New York. Of all the Don Draper mistresses, the free-spirited Joy may have been the youngest of them all.

However, she is the one who aggressively pursues Don, much to his surprise. To add to the oddness of the brief affair, Joy's father, Willie, is the one who introduces them and then casually walks into their room while they are in bed together where he makes reference to the fact that he is attracted to Don. It makes for a rather surreal affair.

15 Bobbie Barrett

Played By Melinda McGraw

This is another instance of Don getting his romantic pursuits mixed in with his business life. Bobbie Barrett (Melinda McGraw) is the wife and manager of comedian Jimmy Barrett (Patrick Fishler). Don meets Bobbie after Jimmy upsets the owner of his sponsor, Utz Potato Chips.

He ires her boldness as she clearly is in charge of her marriage. However, when she makes a move on him, he initially suggests he is not interested though she sees through his lie. It makes for an eventful affair for the two, which includes them getting in a car accident that requires Peggy (Elisabeth Moss) to help out and let Bobbie stay with her.

Perhaps Bobbie's biggest contribution to the series is her advice to Peggy that she cannot win by trying to be a man in the business world but can use being a woman to her advantage. Don ends their Mad Men season 2 relationship when he learns Bobbie has been gossiping about his prowess in the bedroom.

14 Shelly

Played By Sunny Mabrey

Shelly (Sunny Mabrey) is one of the most short-lived Don Draper mistresses and seems to represent the idea that Don does this sort of thing everywhere he goes. Don has a one-night stand with the stewardess when he travels to Baltimore with Sal Romano (Bryan Blatt) in Mad Men season 3. Shelly invites Don and Sal to dinner with her flight attendant friends, but she is gone after a fire alarm evacuates the hotel.

Don is shown to be a massive hypocrite, having an affair with Shelly while on the trip but getting angry at Sal.

However, the real fallout of Don's Baltimore trip was his discovery that Sal is a closeted homosexual, which later led to Romano's dismissal from Sterling Cooper. In that sense, Don is shown to be a massive hypocrite, having an affair with Shelly while on the trip but getting angry at Sal for doing the same thing simply because it was with another man.

13 Suzanne Farrell

Played By Abigail Spencer

Suzanne Farrell (Abigail Spencer) is Sally's teacher who's the last of Don Draper's mistresses before Betty ends their marriage. Despite her hesitation, Suzanne begins an affair with Don, after itting to him and herself that she cannot stop thinking about him. While Don falls for her idealism, she also seems to see through him in ways other women haven't, telling him that she sees a lot of sadness in him.

Suzanne represents someone who is a good person dragged into Don's world of lies and deceit. She is constantly nervous about being caught in public with Don, and not enjoying their time together. Things end abruptly when Betty discovers Don's hidden records that he was really Dick Whitman and confronts him, which immediately puts an end to Draper's tryst with Miss Farrell. When Don calls her to call it off, she asks him if he is okay to which he responds, "Only you would ask about me right now."

12 Candace

Played By Erin Cummings

In Mad Men season 4, Don moved out of his house with Betty and Jon Hamm's problematic ad man took an apartment in Manhattan. Candace (Erin Cummings) is a sex worker Don frequently hires. It is a sign of him slipping further into a dark spiral with his relationships becoming purely transactional. There is also a disturbing moment between the two when Don has rough sex with Candace claiming that he thought she liked it when she objects to it.

Later in season 4, Draper introduces Lane Pryce (Jared Harris) to Candace and her friend to cheer him up when his marriage is on the rocks. They go back to Don's apartment, but Lane notices that Candace seems to have a familiarity with the apartment, realizing that she and Don have some previous connection with each other.

11 Allison

Played By Alexa Alemanni

Allison (Alexa Alemanni) became Don's secretary after Peggy became a copywriter, and, in turn, she became another one of Don Draper's mistresses. Don brings her along when he leaves Sterling Cooper to co-found Sterling Cooper Draper Pryce. Allison succumbed to her attraction to Don and slept with him after the office Christmas party.

She was then heartbroken when Draper pretended like it never happened and gave her cash as a Christmas bonus. Allison is one of Don's affairs that makes him look truly awful. She is shown to be a very effective and successful secretary for him which makes her dismissal from the office all the more telling.

In the aftermath of her leaving, Don is shown to begin writing an apology letter to her which shows that he is aware of his terrible behavior, but eventually discards it. Joan Harris (Christina Hendricks) replaced Allison with the elderly Ida Blankenship (Randee Heller), a sign that Don cannot be trusted to not make the same mistake again.

10 Bethany Van Nuys

Played By Anna Camp

Bethany Van Nuys (Anna Camp) is a friend of Roger Sterling's young bride Jane (Peyton List) with whom Don is set up. It is also noted that she bears a striking resemblance to Don's ex-wife Betty. Despite her youth and charms, of all the Don Draper mistresses, Don doesn't have much chemistry with Bethany.

While he its she is a sweet girl, he shows little interest in her, taking her on only a few dates over the course of several months. However, Bethany on his arm does make a couple of key people in Don's life jealous: Ted Chaough (Kevin Rahm) and his wife run into Don and Bethany at Benihana's, and later, Betty is furious when she finds herself at the same restaurant as Don and Bethany.

In the end, Don writes about Bethany in his journal, lamenting that he knows who she is by this point, and it is not the person he wanted her to be.

9 Alice & Doris

Played By Amy Motta & Becky Wahlstrom

The combination of two very brief affairs with two different women are used to show the further spiraling nature of Don's behavior. When Don wins a Clio Award in Mad Men season 4's "Waldorf Stories," he goes on a bender that lasts for days. Don goes to bed with Alice (Amy Motta), a woman he picks up at a bar while he's celebrating his Clio.

However, when he wakes up in the morning, he is next to a waitress named Doris (Becky Wahlstrom), whom he doesn't recognize. Worse, Doris calls him "Dick," which means he drunkenly calls himself by his secret birth name and not his carefully maintained identity during his blackout tryst with the waitress. In a quick moment with these two women, the show highlights the destructive path Don is on. While he is always reckless, this is a rare instance in which he recognizes it himself.