In the tenth episode of the fifth season, in an episode titled "Christmas Waltz," Joan and Don visit a Jaguar dealership to test drive a car, and subsequently find themselves at a bar discussing their respective current personal woes.
While the flirting between them appears to be more like two friends with similar intellects and of similar levels of attractiveness simply admiring each others beauty, it's not completely clear why they haven't taken their relationship further.
Although Don is (sometimes happily) married to Megan, he has a history of philandering with co-workers - though that seems to be both in the past and out of the question with Joan.
Joan is only a short while removed from being served divorce papers by her occasionally abusive husband, Greg.
There is obvious sexual tension between the two of them, though perhaps that's all it is. The question remains: why have Joan and Don never slept together?
Answer
Christina Hendricks, the actress who plays Joan Harris (née Holloway), alludes to Don and Joan being nothing more than good friends in an interview with GQ. They are two people that respect one another and enjoy each other's company, but that is it. Not to mention that both are "too wise about office politics [Joan and Don sleeping together] into their already-tricky lives at the moment."
Furthermore, she points out that "adding another layer to [Sterling Cooper Draper Price]" would over-pack an already jammed environment, from a structural plot line point of view.
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