Introduction
“You Shouldn’t Kiss Me Like This” – A Tender Turning Point in Toby Keith’s Career
Toby Keith wrote and recorded “You Shouldn’t Kiss Me Like This” as part of his fifth studio album, How Do You Like Me Now?!, released in 1999 after he joined DreamWorks Nashville under producer James Stroud . Issued as the fourth and final single from the album on October 16, 2000, the song quickly became one of Keith’s most beloved ballads .
The song peaked at No. 1 on the U.S. Billboard Hot Country Singles & Tracks chart—maintaining that position for three nonconsecutive weeks starting March 3, 2001—and reached No. 32 on the Billboard Hot 100 . It marked his second consecutive country chart‑topper, following “How Do You Like Me Now?!” and reaffirmed his versatility as both songwriter and vocalist .
Musically and lyrically, the song is a gentle country ballad built around a moment of romantic tension between two friends. Its chorus captures the protagonist’s emotional conflict:
“You shouldn’t kiss me like this unless you mean it like that / ’Cause I’ll just close my eyes…”.
The arrangement favors steel guitar and soft melodies, creating a dreamy, evocative atmosphere that highlights Keith’s emotive vocal delivery .
The music video, directed by Michael Salomon and premiered via CMT on October 19, 2000, presents a narrative twist: a daydream set in a wedding‑reception ballroom ends abruptly with real‑world awkwardness, emphasizing the theme of unrealized longing .
In the context of Keith’s career, the song bridged his polished “90s balladeer” persona and the more assertive, brash style that would come to define him in the post‑9/11 era. Fans and critics alike have noted that it remains one of his most emotionally resonant and enduring performances