Roger divorces his first wife, Mona, after taking up with the much younger Jane Siegel, who briefly worked as Don Draper's secretary. Previously, Roger had a lengthy affair with Joan Holloway, then Sterling Cooper's Office Manager.
Anticipating a costly divorce settlement with Mona, Roger encourages the takeover of Sterling Cooper by London's Puttnam, Powell, and Lowe. When the new managers leave him off a corporate organizational chart, however, Roger believes he's "being punished for making my job look easy." He feels similarly slighted by friends who can't accept his relationship with Jane. "I made a mistake by being conspicuously happy," he tells Don.