Bill has hit rock bottom after his falling out with Virginia. He still has legal problems and he gets into a car accident while drunk. The court orders him to complete community service and attend AA meetings. Meanwhile, Virginia seems to have married Dan, but he is nowhere to be found. 

Bill returns to the office where Betty tells him he needs to move forward with the work without Virginia. Virginia goes to Chicago to meet with Hugh Hefner. She proposes a recurring column for Playboy that he will write on her own without Bill. Hugh is intrigued, but secretly calls Bill out to Chicago. Once Virginia and Bill are in the same room, Hugh says he will only work with them if they remain the team of Masters and Johnson. Bill and Virginia agree to work in the office, but their personal lives will no longer be intertwined.

Meanwhile, Libby refuses to speak to Bill and hires a lawyer to help her with divorce proceedings. She also attends a feminist group where she meets women very different than herself.