The male lead was originally written for John Ritter, but his death stopped Peter Bogdanovich from wanting to make it. When Wes Anderson introduced him to Owen Wilson, he liked him so much that he decided to bring the movie back.
Jennifer Aniston was first offered the role of Delta, but after reading the screenplay, she preferred the part of Jane Claremont. She later advised Bodganovich to cast Kathryn Hahn as Delta and also suggested Will Forte to play Joshua Fleet.
Principal photography lasted 29 days, commencing on July 11, 2013, in New York City. Peter Bogdanovich's original version, titled "Squirrels to the Nuts" lasted 113 minutes. However, he was compelled to change the film (along with its title) in order to get a release, which saw the eventual 94-minute version released to theaters that saw a modified opening and ending, deletions of music (such as the stylings of Frank Sinatra and Tom Petty), and a framing device of an interview that cuts in and out through the film.
She's Funny That Way (2014) originated in the mid-1990s when People reported the film would be going into pre-production, with the title "Squirrels to the Nuts" and featuring Tatum O'Neal in the leading role. Peter Bogdanovich, who had worked with O'Neal on Paper Moon (1973) and Nickelodeon (1976), was quoted as saying "This movie is my gift to her."