I can't believe I didn't notice until Couch Baron's recap pointed it out that the first flashback scene explicitly identified Uncle Mack as "the one that brung you." I feel like this casts Don's later comment that "Sometimes you gotta dance with the one that brung you" in a very different light.
Originally I was imagining that, like others have suggested, it represented Don's attempt to cling to some pretense of fidelity. That is, Don was insisting that their conversation with Ketchup remain purely for show, the same way that his affair needed to exist only in his and Sylvia's heads, lest he blow up an existing relationship that's still very valuable to him. In that sense, dancing with the one that brung you means you hold back something out of loyalty to the person you're supposed to be with.
But if Don used the phrase while thinking of Mack as the one that brung his stepmother then forced her to sleep with him despite the fact that he was "with" her sister, then it's not about loyalty or fidelity at all. Indeed, it's about betraying
one's family and one's long-held beliefs for the sake of a much baser obligation. And, really, that's not unlike what Raymond is asking them to do, in his own pathetic way. It's not like with Mohawk in season 2, where Don had to completely throw them over for a shot at American Airlines (and thus it was
a clear-cut metaphor for marital infidelity). Here, SCDP could have it all, Ketchup and
Beans, were it not for Raymond's completely unreasonable demand that they string Timmy along and betray their own best interests instead.
What does that say about the personal story that the work tale is meant to analogize? If it isn't as clear-cut as "Megan is the one that brung Don, so he should be faithful to her," then who brung who? Maybe Don is sympathetic to Raymond's pathetic plea because he sees himself
as the guy who's afraid of losing his girl to someone else -- to an acting career that will take children out of the picture and render him superfluous as a provider? Thus, just like with Sylvia, he's trying to recreate in the office what he no longer has at home: a scenario in which you're grateful to your "man" for being there for you when you were at your lowest, and you don't need to be snag the Heinz Ketchup account or be a soap opera star to feel content and complete. I'm the guy that brung you, Megan, so why can't that be enough?
Edited by Dev F, Apr 21, 2013 @ 2:31 AM.