In the United States, it peaked at number 47 on the Billboard 200 and was eventually certified gold by the Recording Industry Association of America (RIAA).

In the US, a track from her first album was included, "When He Shines", which was released as a single and peaked at number 30.

You Could Have Been With Me became a top-10 album in Japan, following the use of the track "A Little Tenderness" in a television advertising campaign for Noevir Cosmetics.

On 23 February 2013, British record label Edsel Records reissued Easton's You Could Have Been with Me and Madness, Money & Music in two-disc packages remastered with bonus tracks.

North American editions of the album replaced "Isn't It So" with "When He Shines", and switched the order of tracks 2 and 5 ("You Could Have Been with Me" and "Savoir Faire".)