[1] It continues in the direction of his previous studio album, This Time It's Love, focusing mostly on ballad material.

"[4] The Penguin Guide to Jazz praised the album, writing that it "confirms Elling as the finest singer of his generation.

He opens on Glenn Miller's 'Moonlight Serenade' and turns it into a complex modernist epic, condensed into just four and a half minutes...Curtis Lundy's 'Orange Blossoms in Summertime' becomes a compelling jazz poem that honors the bassist's art and builds into something bigger and more ambitious.

Jazz singers have rarely been drawn to Stephen Sondheim, but Kurt sees the merit in 'Not While I'm Around', from Sweeney Todd.

"[3] The Allmusic review by David R. Adler awarded the album four stars, and described it as "a worthy statement from Elling, who shows yet again that vocal jazz can be more than just easy listening"[1] Flirting with Twilight received a Grammy Award for Best Jazz Vocal Album, the fifth nomination in a row since Elling's debut.