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Don Draper's Women on Mad Men

Person list created by EatMorePez Avatar

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Betty Draper - Don's first wife. (Technically his second, but that's a long story.) They are married for ten years and have three children together. But that doesn't mean he's slept with her the most, does it?

And they hook up once after their divorce. For old times sake. At their son's summer camp. Because that's totally normal.

Midge Daniels - The first of Don's mistresses that we meet. Actually we meet her before Don's wife, but it's safe to assume that he slept with Betty first. Midge is a freelance artist who does work for Don. Their affair ends late in season one. But she returns in season four, strung out on heroin and hitting up Don for money so she and her junkie boyfriend can get their next fix. Don writes her a check and we never see her again.

Average listal rating (137 ratings) 7.6 IMDB Rating 0
Rachel Menken - A client of Don's who he meets in the pilot but doesn't sleep with until episode 10, after he and Midge have called things off. Don is apparently a one-mistress-at-a-time kind of guy.

Bobbie Barrett - She is the wife and manager of comedian Jimmy Barrett, an insult comic whom Don's firm uses in their advertisements for Utz Potato Chips. They have an affair and then get into a car accident that threatens to expose their tryst. The two resume their affair after a brief hiatus following the accident, but Don breaks it off completely and abruptly, when Bobbie reveals to him that she and other women with whom Don has had affairs have been discussing his prowess as a lover. This is the first of Don's affairs that Betty knows about, because Bobbie's husband told her. Helluva guy.

Average listal rating (256 ratings) 7.6 IMDB Rating 0
Joy - a free-spirited bohemian nomad, who encounters Don, during a business trip to Los Angeles in "The Jet Set" episode. Don ditches his colleague, Pete Campbell, for several days so he can play sex games with Joy. Can you blame him? Pete Campbell is the worst.

Average listal rating (69 ratings) 7.6 IMDB Rating 0
Shelly - A stewardess Don meets on a flight in the third season premiere. Of course Don Draper can bed a stewardess he meets on an airplane. Of course he can.

Suzanne Farrell - She is the teacher of Don's daughter Sally, and the final mistress Don had during his marriage to Betty.

Allison - Don's young, competent secretary. Unfortunately for her, she worked for Don Draper before anyone had ever heard of a sexual harassment lawsuit. Drunken Don bedded Allison, then pretended it didn't happen and gave her a $100 bonus to help her forget. She didn't forget. She remembered it all and threw an ashtray at Don's head to help him remember. That was her last day Sterling, Cooper, Draper & Pryce. Poor Allison.

Average listal rating (241 ratings) 7.7 IMDB Rating 0
Bethany Van Nuys - Don went on three dates with her, but they never slept together. But he did get to second base in the back of a cab. Don goes to see a call girl after Bethany puts up the stop sign.

Candace - Said call girl. It is obvious that Don regularly sees her as she knows exactly what he likes: slapping.

Average listal rating (5 ratings) 6.6 IMDB Rating 0
Alice - She and Don met at the Clio awards. They got drunk and she "serviced" Don while humming the Star Spangled Banner. A true patriot.

Doris - After getting the star-spangled treatment from Alice, Don wakes up two days later with Doris, a waitress he has no memory of. But she apparently knows him well enough to call him "Dick." At this point, most people might find the nearest AA meeting. Not Don though, he soldiers on.

Average listal rating (74 ratings) 7.2 IMDB Rating 0
Dr. Faye Miller - a strategist for a consumer-research company who Don has an above board relationship with after he and Betty divorce. The first woman who appears to be Don's equal in both the bedroom and the boardroom.

Megan Draper (née Calvet) - Don's secretary who becomes his second wife. But he forgot to dump Dr. Miller before proposing to Megan. Whoops.

Sylvia Rosen - The wife of Don's friend and neighbor, Dr. Arnold Rosen. Don has an affair with her after marrying Megan. The affair ends for good when Don's 13-year-old daughter, Sally, walks in on them. Awkward . . .

Lee Cabot - A wealthy widow Don meets on a red-eye flight from LA to New York in the season seven premiere. Upon landing she suggests they "share a cab" back to her place, but amazingly, Don turns her down.

Amy - A California friend of Megan's. After a party in their LA house, Megan suggests or should I say, demands, that they have a three-way. Don is reluctant at first, but then says, "What the hell."

Average listal rating (10 ratings) 7.1 IMDB Rating 0
Tricia - A stewardess who leaves a message with Don's answering service that she's in town on a layover. Don of course calls her over to his apartment, where she drops a glass of red wine on his white carpet. He just throws a blanket over the wine stain and has his way with her.

Diana - A waitress in a coffee shop who Don thinks he's met before. "You don't need a line, I know why you're here," she tells him. He then proceeds to take her in the alley behind the diner while she is on a smoke break.

Eve - Don's final conquest on the series finale.  She tried to lift his wallet. Don caught her but gave her some cash anyway. What a gentleman. 

The many women Don Draper has slept with on Mad Men, in chronological order.

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