The album was preceded by the release of its lead single, "Western Wind", which was followed by "Beach House", "Talking to Yourself", and the title track.

Jepsen spoke to The Guardian that she was writing songs over Zoom alongside longtime collaborator Tavish Crowe.

It excited me to have those moments of flirtation on the [new] album, but also broaden the spectrum of what the subject of a pop song was allowed to be...[3]In an interview with The Ringer, Jepsen teased the possibility of releasing a "side B" companion project to The Loneliest Time, as was done with her previous two albums, Emotion (2015) and Dedicated (2019), stating that "there's 65 [B-sides] that I've listened to that I could make something of...".

[9] Rob Sheffield of Rolling Stone wrote "The Loneliest Time is her most "emotionally adventurous" music yet—"high-gloss post-bubblegum synth-pop that packs a serious punch even at its fizziest.

"[16] Hannah Mylrea of NME awarded the album four out of five stars, writing that The Loneliest Time "sees Jepsen's now signature sonics infused with more expansive influences, although never deferring too far from the tried and trusted sounds of past.

[20] Gem Stokes of Clash said the album is "a far cry from the saccharine star that launched Jepsen's career but proves her musical pliability.