The Most WTF? Moments of 'Mad Men' Season Six

How Don Draper and co. blew our minds this season

Don and Sylvia's Hotel Room Tryst

Jon Hamm as Don Draper and Linda Cardellini as Sylvia Rosen on Mad Men
Courtesy of AMC

Episode Seven, "Man With a Plan"

Sylvia Rosen is no Anastasia Steele, that's for sure. A couple of days locked in a hotel room, commanded to give Don his shoes on her hands and knees and being told "You exist in this room for my pleasure" drained the fun and excitement out of this affair faster than Sylvia could even utter a safeword. This wasn't the first time Don has exhibited D/S tendencies (remember when he tied Bobbie Barrett to the bed?), but his desire to treat Sylvia as little more than an object is what forced her to put the kibosh on their arrangement. As she prepares to return to her cuckolded husband and stop seeing Don once and for all, she chastises him for degrading her: "It's easy to give up something when you're ashamed."

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