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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.
joan don bar
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?

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I think the only answer here is "because the writers haven't written it". –  DisgruntledGoat May 31 '12 at 9:04
    
I don't think we have enough information to judge they haven't already. Both predate the series as co-workers at Sterling Draper. We've caught this story in the middle, and it may be we just haven't seen the history sufficiently. –  wbogacz May 31 '12 at 11:56
    
@wbogacz - From flashbacks it's clear that Joan and Roger were having an ongoing affair when Don tricked Roger into hiring him. –  jfrankcarr May 31 '12 at 14:36
    
None of those flashbacks included Don, nor precluded the possibility of a Don/Joan relationship. The gynocologist she sends Peggy to is an implied relationship, and demonstrates she's capable of compartmentalizing men. Maybe Don is just another compartmentalized relationship. We just don't know. –  wbogacz May 31 '12 at 17:09
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2 Answers

up vote 3 down vote accepted

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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According to Matt Weiner, the show's creator, Don is," Looking for his" in the women he sleeps with. Joan just doesn't fill that void for him.

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