Mad Men
Don (Jon Hamm, left) had an affair with Sylvia Rosen (Linda Cardellini, right) throughout Season 6 of "Mad Men." AMC

Throughout seven seasons of “Mad Men” -- which begins airing its final episodes on April 5 -- Don Draper (Jon Hamm) has become arguably the most infamous philanderer in television history. From Betty (January Jones) to Megan (Jessica Paré) and everyone in between, it can sometimes be hard to keep track of every indiscretion in the character’s story.

Here is a list of all the wives, mistresses and hookups that Don has had throughout “Mad Men” in order of the show date of each steamy encounter:

1. Midge Daniels (Rosemarie Dewitt) – Season 1, Episode 1 (“Smoke Gets in Your Eyes”)

Before fans ever saw Betty, there was Midge. The Village artist lured Don’s more adventurous side throughout much of the first season, but he became frustrated that he could never have her all to himself. Eventually, she fell for another man and the relationship ended, but Midge would later return in Season 4 as a drug addict to beg Don for money.

2. Betty Draper (January Jones) – Season 1, Episode 1 (“Smoke Gets in Your Eyes”)

Don’s marriage to Betty – which lasted three seasons on the show – was largely joyless and unhealthy. However, no relationship more defined the character as fans watched him struggle to preserve a hollow marriage despite the truth that they were truly strangers. Even when the couple had their rendezvous hookup at Bobby’s summer camp in Season 6 they seemed to recognize that they were wrong for each other.

3. Rachel Menken (Maggie Siff) – Season 1, Episode 1 (“Smoke Gets in Your Eyes”)

Though they do not immediately sleep together, the sexual tension between Don and Rachel in the pilot was palpable. More so than any other of Don’s lovers from Season 1, Rachel was a true equal, calling him on his lies and seeing the real person behind the suave front. However, when Don impulsively suggested they run away together the affair came to end.

4. Bobbie Barrett (Melinda McGraw) – Season 2, Episode 3 (“The Benefactor”)

Don’s affair with the manager/wife of comic Jimmy Barrett (Patrick Fischler) bordered more on friendship than the majority of Don’s mistresses – or even his wives. However, it also brought out the character’s most reckless side. Things got hairy after a drunken car crash put the couple in a precarious position with their respective spouses, but it was over for good when Don found out that Bobbie had been gossiping about their relationship around town.

5. Joy (Laura Ramsey) – Season 2, Episode 11 (“The Jet Set”)

This one-episode affair – while Don was MIA in California – was most notable for the couple being caught by Joy’s shockingly approving parents. Fans never saw the free-spirited bohemian girl again.

6. Shelly (Sunny Mabrey) – Season 3, Episode 1 (“Out of Town”)

The ever-classy Don hooked up with engaged stewardess after a flight to Baltimore. Meanwhile, Betty was pregnant at home with their third baby.

7. Suzanne Farrell (Abigail Spencer) – Season 3, Episode 2 (“Love Among the Ruins”)

It was a particularly inappropriate move – even for Don’s low standards – when the ad man started seeing his daughter’s teacher. Most of Don’s flings have taken place in the city, but with Suzanne out in the suburbs, the secrecy required of the affair took its toll on Suzanne until Don eventually broke things off.

8. Candice (Erin Cummings) – Season 4, Episode 1 (“Public Relations”)

Candice was the prostitute who slapped Don – who then asked her to do it harder. That shocking moment was the extent of this one-scene relationship.

9. Bethany Van Nuys (Anna Camp) – Season 4, Episode 1 (“Public Relations”)

At this point divorced from Betty, Bethany was Don’s first aboveboard date on the show. The much-younger girl tried hard to make things work for Don, but he lost interest relatively quickly.

10. Allison (Alexa Alemanni) – Season 4, Episode 2 (“Christmas Comes But Once a Year”)

Allison had been a mainstay on the show since Season 1 and one of Don’s most loyal and capable secretaries, but the relationship soured when a drunken Don took advantage of Allison when she brought his children’s Christmas presents to his apartment. When he tried to smooth things over with a cash bonus the next day, she left the office in tears.

11. Alice (Amy Motta) – Season 4, Episode 6 (“Waldorf Stories”)

This was a quick hookup after the CLIO Awards, notable for its patriotic undertones. Saying anything more would be unsafe to print here.

12. Doris (Becky Wahlstrom) – Season 4, Episode 6 (“Waldorf Stories”)

Another post-CLIO Awards fling, but fans did not get to see much of this one. Don woke up in bed next to the waitress without remembering who she was or how they got there.

13. Dr. Faye Miller (Cara Buono) – Season 4, Episode 8 (“The Summer Man”)

In many ways, Faye is the woman Don should have chosen – instead of Megan. Not since Rachel Menken had he had a true intellectual match and the researcher was more than interested in things getting serious. However, Megan’s knack with Don’s kids won him over and left Faye on the outs.

14. Megan Draper (Jessica Paré) – Season 4, Episode 11 (“Chinese Wall”)

What started as another secretary fling turned into Don’s second marriage after Megan accompanied him on a trip to California to help watch his kids. What followed – until what appeared to be the end of the relationship in the Season 7 midseason finale – was a fascinating attempt at making a marriage work despite striking personality differences and a generational gap putting a strain on the relationship. To the marriage’s credit, Don seemed serious about changing for Megan for stretches, but in the end old habits came back to doom the couple.

15. Andrea Rhodes (Mädchen Amick) -- Season 5, Episode 3 (“Mystery Date”)

While the actual affair may have taken place off screen and years earlier, Andrea created an awkward moment when she ran into Don – and Megan – in an elevator in the Time-Life building. Even more awkward was Don’s dream of strangling the woman to death.

16. Sylvia Rosen (Linda Cardellini) – Season 6, Episode 1 (“The Doorway, Part 1”)

Don’s mistress over the course of Season 6 was Sylvia, the wife of his doctor friend and neighbor. This was a particularly sad affair as Don’s once hopeful – and faithful – marriage to Megan started to crumble. It also made waves in Don’s relationship with his daughter as well, after Sally (Kiernan Shipka) caught the couple in the act.

17. Amy (Jenny Wade) – Season 7, Episode 5 (“The Runaways”)

Amy was the third leg in the ménage à trois that Megan put together for Don as a last ditch attempt to save the marriage. She did not stick around for long after – nor did the marriage.

Who is your favorite woman from Don's life? Tweet your thoughts to @Ja9GarofaloTV.

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