In Mad Men Season 5′s Tea Leaves, Roger is upset after Pete embarrasses him in a meeting. Don observes this happening and goes down to the hall to pacify Roger. The two have a drink in Don’s office and Roger vents to Don about his frustrations. Then Don tells Roger that Betty might have cancer. They discuss it, quite seriously, for a couple of moments, and Don actually opens up to Roger about his fears of losing the mother of his children.
It’s an interesting scene to watch. I initially thought Don approached Roger strictly to offer Roger comfort. But seeing it again, I realize that Don wanted some comfort himself—or at least the comfort that comes with sharing a confidence. We see Don and Roger fight sometimes and at other times we see them getting along great. But when they’re getting along, it’s usually a fun, lightweight sort of friendship. Two office buddies/partners who play the same game. This scene went a little deeper. Does Don at times want a friend? He always seems so solitary, so deliberately disconnected from everyone around him. But he had moments of friendship with Arnold Rosen in Season 6, and at times he seems to enjoy having a real connection.
I really enjoyed this moment between Don and Roger, and wouldn’t mind seeing more moments like this. It’s rare for Don to let someone know that he needs to talk. I’m not sure if that will ever change. He’s very used to keeping his guard up.