The television series Mad Men is critically acclaimed despite grievous flaws as a drama. Its immense popularity is important psychological data and needs to be explored from the vantage of the dynamics of deception, including motivation, appeal and consequences for relationships and the self. The show's creator is inspired by John Cheever, the depth of whose complex characterizations is contrasted to the lures of the show. The parallel between the manipulations of authenticity inherent in advertising, the relationships between those who are involved in it and the relationship the show establishes with its audience is studied through two contiguous brief scenes that portray multiple reverberating deceits. These characters in these scenes are understood as creating both longing and disappointment at multiple levels. The psychic costs for both the deceivers, those deceived, as well as witnesses to the deception are fundamental.