Handler talks with her family and friends (including Jason Biggs and Mary McCormack) about how her views on marriage have changed during her life and also interviews a number of married couples, professionals who work with marriage (e.g. wedding planners, marriage counselors, matchmakers), and kids about marriage.

Handler talks with fellow comedians (including Margaret Cho, Aasif Mandvi, and Michael McDonald) about racism and racial humor in the United States, visits a former plantation, and explores some of Los Angeles' ethnic neighborhoods with Loni Love. She speaks with Al Sharpton to talk about race and race relations, and meets with a group of people representing several civil rights organizations to talk about the boundaries of racial humor. She also speaks with Matthew Heimbach about the rise of white-nationalism.