Mad Men is disturbing to post-millennium viewers, particularly those of a “certain” age, on three counts. First, it invokes a particular historical context of gender oppression; second it captures the prevailing post-War injunction that emotional distress is unseemly and distasteful; and third, it captures the zeitgeist's celebration of surface over substance in relationship. However, just as disturbing as these historically situated interpersonal premises is the niggling question that each relationship pairing and each episode leaves with the viewer. To wit: How much of the disconnection and the unrequited longings are reflective of a particular historical era, and to what degree do they reflect timeless aspects of character and relationship? Thus Mad Men provides an exquisitely rendered sociocultural tableau in which the viewer struggles, however articulated or not, with one of the essential knots of psychoanalytic as well as couples treatment: the complicated interpenetration of culture and character, of time and timelessness.