For about three years, Big Sean and Jhené Aiko dated one another on-and-off, but in March 2019, Aiko confirmed that they broke up.[1] "Single Again" marks the first collaboration between them ever since.[2]
Lyrically, Big Sean mulls over the end of his relationship with Aiko and unnecessity of entirely blaming the shortcomings on the other person.[3] He also recognizes the importance of taking time for himself to focus on his own needs, as well as the impact on his mental health resulting from the breakup.[4] Prior to releasing the song, Sean tweeted lyrics of the song,[2] as well as a message that details the song's meaning and the importance of finding solace in a relationship with himself:
I never knew that I didn't know how to be alone in life. I always would find so much joy n happiness in a relationship or being with friends, but I didn't know how important it was to be in a relationship with yourself.[5]
Music video
A music video was released on July 29, 2019. Directed by Lawrence Lamont with cinematography by Jon Chema, the video stars Ryan Destiny, Keith Powers and Haha Davis, and follows a recently separated couple. Big Sean also raps in the middle of a street and inside a car surrounded by fans,[6] and finds himself being put on trial and going to prison for infidelity.[7] A shorter music video was released on August 26, 2019.