Bobbie Barrett

Don's sexual violation of Bobbie while at dinner with his wife might be the most reprehensible thing he's done in four seasons of reprehensible things. It's not consensual or sexy, and the most dysfunctional thing about it is that Bobbie is strangely enthralled by his hate-sex, revealing an intensely jaded woman so used to dealing with powerful men that she embraces their misbehavior and even revels in it. Both of them are fucked up, but they seem almost mutually fucked up, and unlike Allison, Bobbie seems to go into her fling with Don with eyes wide open. She knows exactly how terrible he is, and disturbingly, that appeals to her.