Songfacts®:

• Though better known for singing of his hedonistic bed-hopping, The Weeknd is not immune to falling in love. On "Here We Go... Again," he croons of having an affair with a movie star. The lyrics reflect an unusually emotionally vulnerable Abel as he grapples with falling for someone he knows will break his heart.
  
  'Cause it's never what it seems
  But you'd rather love and lost with tears
  Than never love at all
  So here we go again
  
  The Weeknd elects to ignore the risk of heartbreak and take another emotional roller coaster ride. He reasons his choice by referencing the saying coined by the Victorian poet Alfred Lord Tennyson: "Tis better to have loved and lost than never to have loved at all."
• Many fans believe the movie star The Weeknd is singing about is Angelina Jolie. Rumors of a relationship between the two circulated in 2021 after paparazzi spotted them at multiple dinner dates in Los Angeles.
• Tyler, The Creator takes the baton in the second verse, expressing skepticism about the institution of marriage. Though he's fallen in love with someone, he's dubious about the relationship lasting and doesn't want to pay out for a divorce. The only way he'll go ahead with a wedding is if his lover signs a prenuptial agreement.
• Bruce Johnston of The Beach Boys contributed to the track. Johnston did the vocal backdrop arrangement and sang the background "Ooohs" with Christian Love, son of The Beach Boys' Mike Love.
• The Weeknd and Bruce Johnston co-produced the song with:
  
  Frequent Chris Brown producer Brian Kennedy ("Forever," "Don't Wake Me Up"). Kennedy also helmed Rihanna's "Disturbia," which Breezy co-wrote.
  
  Rex Kudo, whose resumé also includes collaborations with Nicki Minaj ("Run & Hide") and Post Malone ("Go Flex").
  
  Benny Bock and Charlie Coffeen also helped with the production.