Songfacts®:

• In this song, Rimes explains how to kiss a boy after he first says "I love you." As the song goes on, the euphoria gives way to doubt, then heartbreak as he turns cold. When she kisses the boy at the end, it's a peck on the cheek to say goodbye.
• Two top Nashville writers, Lori McKenna and Barry Dean, teamed up to write this track. In a Songfacts interview with Dean, he said, "That's a case where I thought, That would be an interesting thing to write a song called 'How To Kiss A Boy,' and really go through all the different kinds kisses that go into a relationship. But I knew Lori would know how to keep us honest. And she'll have an insight that's deeper than others. So, I showed this to Lori to see if she'd write it with me, and that night, and I think she knew I would know what she meant. I would know what her heart was feeling."
• This piano ballad was the second single (following "The Story") from Rimes' 16th album, Remnants. This was her first album under a new deal with RCA, following 20 years at Curb Records.