In a 2023 interview with Filmmaker magazine, Nicole Holofcener spoke about the personal thoughts and feelings that inspired the film: "A lifetime of wondering if people are lying to me inspired the idea. And when they don't lie, can I cope with that? I guess my experience of being vulnerable to other people's opinions about me and my work, and the fact that my work is so autobiographical. My movies feel like they're me. I really feel like they are so close to my personality and values and the things I think and worry about. And the characters-at least one usually-are so clearly based on me. And if they don't get it, can they get me? Can I also live with the possibility that they don't get it, or like it, and still love me? But yeah, sometimes I can cope with it well, and sometimes I can't. I still want approval, of course. Don't we all?"
Amber Tamblyn and David Cross are married in real life; this is the first film in which they both appear.
Julia Louis-Dreyfus and Jeannie Berlin play daughter and mother in the film; in real life, the actors are 11 years apart in age.
Kenneth Tigar, who briefly appears as one of Don's older patients, regularly appeared as one of the regular clients on original The Bob Newhart Show (1972).
Cinematographer Jeffrey Waldron said, "I worked to build a natural, inviting New York look that didn't distract from the unfolding story, but brought cinematic punctuation to its important human moments."