All the Women Don Draper Doesn’t Sleep With on Mad Men
Don Draper sleeps with a lot of women. It’s one of his things. You know, like getting drunk at lunch, or committing identity fraud. But throughout the course of Mad Men’s six-plus-season run, there have also been some moments where flirtation shockingly did not lead to copulation, moments where a lingering glance and a brush of fingertips have not resulted in an adulterous tryst. On Sunday’s episode, Neve Campbell cameoed as one of these rare beasts: a woman whom Don flirts with and ultimately does not have sex with. Here’s a look at all the other times Don didn’t seal the deal.
* This slideshow initially said that Phoebe and Bethany were in season 3. As a commenter pointed out, they were characters in season 4.
After hiring them on the spot at an SCDP casting, Roger invites the 19-year-old twin models to his office for a private celebration. While Roger is te...
After hiring them on the spot at an SCDP casting, Roger invites the 19-year-old twin models to his office for a private celebration. While Roger is testing his cardiovascular strength by riding Twin One around the office like a pony, Twin Two receives only a reluctant kiss from Don. To her line about having been around the block a few times, a glassy-eyed Don responds, “I don’t even think I could get out of the driveway.” Poooor Don.
Don has too much on his mind to go home with the waitress from the Asian restaurant early in season two, despite engaging in a serious flirting sessio...
Don has too much on his mind to go home with the waitress from the Asian restaurant early in season two, despite engaging in a serious flirting session to the strains of "Sukiyaki." We hope he left a big tip.
When the future ex–Mrs. Roger Sterling is hired to be Don’s secretary, she practically throws herself at him, but her good looks (and all the shirts s...
When the future ex–Mrs. Roger Sterling is hired to be Don’s secretary, she practically throws herself at him, but her good looks (and all the shirts she buys him from Menkens) prove to be of zero interest. Thankfully Roger is there to pick up the pieces.
After sharing some barbituates with two young hitchhikers he picks up, it appears things might get a little weird. Instead, Don hallucinates his alcoh...
After sharing some barbituates with two young hitchhikers he picks up, it appears things might get a little weird. Instead, Don hallucinates his alcoholic father and gets punched in the head and robbed. Drugs 1, Don 0.
When Don gets an attractive new neighbor, it usually means something untoward is going to happen. Not so with bob-sporting nurse Phoebe, who nobly reb...
When Don gets an attractive new neighbor, it usually means something untoward is going to happen. Not so with bob-sporting nurse Phoebe, who nobly rebuffs his drunk advances, and then gets uncermoniously fired from her babysitting gig when Sally attempts to imitate her haircut.
Don goes on a number of dates with this young, assertive Betty look-alike, but for some reason, the sparks just aren’t there. She plays hard to get, t...
Don goes on a number of dates with this young, assertive Betty look-alike, but for some reason, the sparks just aren’t there. She plays hard to get, teaches him to use chopsticks, and goes down on him in the back of a cab before Don decides that he’s found out all there is to know about her. “She’s a sweet girl, and she wants me to know her, but I already do,” Don writes later.
While it always remains something of a mystery, Don's accidental relationship with his alter ego's widow turns out to be one of the show's most meanin...
While it always remains something of a mystery, Don's accidental relationship with his alter ego's widow turns out to be one of the show's most meaningful — and its least salacious.
Although nothing ever happens with Anna, Don can’t resist the charms of her beautiful, bohemian niece Stephanie. However, his seduction attempt is cut...
Although nothing ever happens with Anna, Don can’t resist the charms of her beautiful, bohemian niece Stephanie. However, his seduction attempt is cut short by Stephanie's poignant reveal that her aunt is dying of cancer.
Realistically, Don was probably never going to sleep with the very young groupie he meets at a Rolling Stones concert (we hope), but his impromptu mar...
Realistically, Don was probably never going to sleep with the very young groupie he meets at a Rolling Stones concert (we hope), but his impromptu market research session certainly toes the line between paternal and inappropriate.
While Edwin, Roger, and Pete all partake of the offerings at a local brothel, Don prefers to nurse his drink alone, despite being popular with the emp...
While Edwin, Roger, and Pete all partake of the offerings at a local brothel, Don prefers to nurse his drink alone, despite being popular with the employees there (as Roger puts it: "Jesus, Don, even in this place you're doing better than us"). It ain't easy being Don.
After a flirtatious, emotion-filled night at a bar together, it seems that Don and Joan might finally act on their long-dormant sexual tension. Instea...
After a flirtatious, emotion-filled night at a bar together, it seems that Don and Joan might finally act on their long-dormant sexual tension. Instead, Don leaves cab fare, tips his fedora, and says, "Good night, sweetheart." For once, a true gentleman.
"Are you alone?" asks the beautiful woman in the dreamlike sequence that concludes season five. Don's eyes say yes, but what happens next, w...
"Are you alone?" asks the beautiful woman in the dreamlike sequence that concludes season five. Don's eyes say yes, but what happens next, we'll never know: Matthew Weiner pulls a David Chase and cuts to black.
Don and Megan turn down the offer to have group sex with Megan's co-star Arlene and her husband Mel. So much for the swingin' '60s.
Don seemed all ready to get frisky with this Betty-esque blonde at a party in California, until a hallucination of a pregnant, hippie-clad Megan led h...
Don seemed all ready to get frisky with this Betty-esque blonde at a party in California, until a hallucination of a pregnant, hippie-clad Megan led him headfirst into the swimming pool.
When Neve Campbell showed up as Don's airplane seatmate in season seven's premiere, it seemed we were destined to see the Party of Five star in some s...
When Neve Campbell showed up as Don's airplane seatmate in season seven's premiere, it seemed we were destined to see the Party of Five star in some state of mile-high undress. Yet while a shared armrest led to some shared intimacies, Don ultimately decided to turn down her advances. Is this the beginning of a whole new Don? We remain skeptical.
There has always been a certain element of will-they-won't-they hanging over Don's relationship with his protégée Peggy; yet so far, the...
There has always been a certain element of will-they-won't-they hanging over Don's relationship with his protégée Peggy; yet so far, the show's central odd couple has managed to keep their relationship platonic (if not always professional) and they probably always will.
Photo: Jordin Althaus/AMC
