Throughout this confrontational soundtrack, Taylor addresses and mocks all the rumors that surround her professional and personal life. In “Who’s Afraid of Little Old Me?,” she highlights how the media constantly downsizes her, evidently through her repetition of “little old me” as she refers to herself. This song shares similar sentiments to previous tracks in Taylor’s discography, namely “the last great american dynasty” and “mad woman” from folklore, “Look What You Made Me Do” from reputation, and “Miss Americana & The HeartBreak Prince” from Lover.

The song echoes many instrumental and vocal similarities with her previous album reputation, which is rumored to be the next rerecording following this album. A large part of reputation discusses the struggle and backlash she faced from the media and people during her 3-year hiatus. In an effort to show that not a lot has changed since then, Taylor details receiving the same comments now as back then.

Taylor writes this song amidst her new relationship with Travis Kelce. Fans believe this album was written in her immediate post breakup period from Joe Alwyn. During that time, many rumors came out about her possible relationship with The 1975 lead singer Matt Healy, feud with Olivia Rodrigo, a possible conflict with Ticketmaster, and allegations that her new relationship was a PR stunt.

The title possibly references the 1966 film/1962 play by Edward Albee “Who’s afraid of Virginia Woolf?,” a film that explores the complexities of a failing marriage.