Bassett is believed to have dated his High School Musical: The Musical: The Series
co-star Olivia Rodrigo during the filming of the show in 2019 before splitting in early 2020. Later that year, rumors started that Bassett was seeing another Disney star, Sabrina Carpenter. When Rodrigo released "Drivers License
" on January 8, 2021, fans figured it was about her heartache over breaking up with Bassett and his relationship with The Girl Meets World
actress. Many also believe "Lie Lie Lie" and "Only a Matter of Time" are his take on romantic entanglement. In both songs, the singer doesn't name names but calls the subject "darling," implying she is a woman.