Introduction
“You Shouldn’t Kiss Me Like This” is a tender country ballad written and recorded by American singer‑songwriter Toby Keith. It was issued on October 16, 2000 as the fourth and final single from his fifth studio album, How Do You Like Me Now?! which had been released in November 1999 .
Recorded in 1999 and produced by James Stroud alongside Toby Keith, the song is a melodic, emotional departure from Keith’s more upbeat hits of the same era . Clocking in at approximately 3:42 in length, it features smooth vocals over traditional country instrumentation, marking one of his most beloved ballads .
Upon release, “You Shouldn’t Kiss Me Like This” climbed the charts to become one of Keith’s signature hits. It reached No. 1 on the Billboard Hot Country Singles & Tracks chart, where it held that position—non‑consecutively—for three weeks, and it also crossed over to hit No. 32 on the Billboard Hot 100 . Despite being the fourth single, the song displayed strong longevity and resonance with audiences, ultimately ranking No. 4 in the year‑end U.S. Country Songs chart of 2001 .
The music video, directed by Michael Salomon, premiered on October 19, 2000 via CMT. It dramatizes a bittersweet storyline featuring a young man and an older woman at a party—a narrative twist ending reveals it as a daydream, matching the emotional bittersweetness of the lyrics .
Lyrically, the song explores the emotional intensity that erupts when two friends cross an unspoken line. The chorus—“You shouldn’t kiss me like this unless you mean it like that”—captures the confusion, longing, and risk inherent in that fleeting moment of connection .
In sum, “You Shouldn’t Kiss Me Like This” stands out as a standout ballad in Toby Keith’s catalog, combining evocative songwriting and compelling vocal delivery. It underscored Keith’s range as an artist at the turn of the millennium and remains a beloved classic in country music circles.