A Compilation of Don Draper’s Indiscretions Concerning the Female Sex

TVThis spring I sort of binge watched Mad Men.  I had no intention of binge watching it but Netflix was cancelling it as of mid June.  Man Men isn’t an easy show to binge watch because it is filled with nuanced behavior and speech. It is also kind of dark but I managed to watch about 1.5 per night.

Since I had seen the series before, I figured I would add a bit of fun to my viewing schedule by giving myself a task.  I decided I would count how many “encounters” Don Draper had with women over the course of the entire series which explains the title of this blog post. It was critical to pinpoint the exact indiscretion I was tracking in the title to this post since Don seemed to engage in so many.


Season 1:

Don is married to Betty Draper

  • Midge, the graphic artist
  • Rachael Menken, the department store owner

Season 2:

Don is married to Betty Draper

  • Bobbie Barrett, manager and wife of a well known comedian
  • Joy, a young girl in California living a jet set version of a vagabond life

Season 3:

Don is married to Betty Draper

  • Shelly, an airline stewardess (that was the job title then). You only saw her once but you got the idea they squeezed each other in during layovers
  • Suzanne Farrell, Don’s daughter’s teacher.

Season 4:

Don is now divorced from is wife, Betty, so he makes up for any lost opportunities

  • A prostitute he sees regularly, name not mentioned
  • Allison, his secretary
  • A woman from an ad agency, a one night thing
  • Doris, another one night thing
  • Bethany, a friend of Jane who is Roger’s wife
  • Dr. Faye Miller, a psychological consultant under contract with Don’s firm
  • Meagan Calvet, his secretary

Season 5:

Don is now married to Meagan, his former secretary. He actually behaves himself for this whole season.

Season 6:

Don is married to Megan.

  • Sylvia Rosen, his neighbor downstairs
  • Betty (Draper) Francis, his former wife

Season 7:

Don is now separated and eventually divorced from Meagan

  • Another random stewardess
  • Diana, a waitress


8 thoughts on “A Compilation of Don Draper’s Indiscretions Concerning the Female Sex

  1. Quite a list. I didn’t realize it was that many and didn’t remember about betty in season 6.

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    1. Well it is an amazing show to watch for its authenticity of the times as well as for the characters and whole story.


  2. While impressive, I thought there would have been more women and the meet ups would have been longer in time and/or substance. Amazing how important overall perception is in any situation! He wasn’t having as much fun as I thought he was having.


  3. I watched Mad Men religiously as it came out and loved it (especially having worked in the orbit of advertising). I always got a kick out of the pricey artwork in Robert Morse’s office that changes yearly with the art scene (Rothko et al). Ever see the “Thirty Rock” episodes with John Hamm as a guest? They thoroughly send up his good looks and sex appeal. He plays a klutzy surgeon who is also a total dufus. At some point he manages to cut off both his hands and then has hooks. Tina Fey falls for him and it’s one disaster after another (and the sex is terrible). Hilarious! Thanks Diane!


  4. I was getting a kick out of Cooper’s office art. I do think Jon Hamm is a nice looking man but the John Slattery type appeals to me much more. Next time I will track Roger’s escapades!


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