Songfacts®:

• "Dear Miss Holloway" is a wistful ode to a one-sided love, inspired by frontman Murray Matravers onetime crush on a teacher.
  
  Maybe in another life
  We could try to roll the dice, and get it right
  
  Matravers laments how the romance didn't work out and wonders whether, given different circumstances, things might have been different. "I think it showcases our ability to tell stories and weave narratives into music," Matravers told Apple Music. "When we came up with the melody and the lyrics for the chorus, we were pissing ourselves laughing. It was such a pastiche of Bee Gees or ABBA or something. It has such a cheesy feel to it, but for some reason it just felt so good and so right."
• Matravers duets with Brockhampton's Kevin Abstract on the track. In his verse, Abstract reflects on his onetime dreams about his future and how they worked out. Their collaboration came about when Matravers was in LA and hit the former Brockhampton frontman on Twitter. The two met up in January 2022, and after they played each other their upcoming music, Abstract asked to cut a verse for "Dear Miss Holloway" right there and then. "Kevin raps about expectations versus reality, choice, and regret," said Matravers.
• Easy Life released "Dear Miss Holloway" as the second single from Maybe in Another Life... The song is also the cornerstone of the record (the chorus contains the album title).
• Murray Matravers, Kevin Abstract, and Easy Life multi-instrumentalist Sam Hewitt wrote "Dear Miss Holloway" with former Dog Is Dead singer Rob Milton and Los Angeles-based songwriters Gianluca and Alessandro Buccellati. Milton is singer-songwriter Holly Humberstone's right-hand man, and Gianluca Buccellati is British singer Arlo Parks' primary producer.
• Gianluca and Alessandro Buccellati also produced the track along with Flange Jr. (Easy Life's "BEESWAX").
• Sam Hewitt played the alto saxophone and arranged the horns. The other wind instrument musicians on the song are:
  
  Trumpet: Ewan Whyte and Aaron Wood
  Trombone: Viva Msimang
  Tenor saxophone: Emma Johnson
  Baritone saxophone: Andrew Cox