A remix version with producer Dupri, and rapper Da Brat appeared as a bonus track on Monica's 1998 CD single, "Angel of Mine".

[2] EMI flew Savage to Atlanta to co-write a song with Dupri for the South Park: Bigger, Longer & Uncut soundtrack, which was expected to be recorded by singer Janet Jackson, but when Savage began working with Dupri, they decided to focus first on writing a song for Monica, which resulted in "The First Night".

[2] The song samples the dark, bassy piano chords intro section from American singer Diana Ross's "Love Hangover" (1976).

[3] Monica commented about the song in a 1998 interview with MTV News: "'The First Night' is not an experience of mine, but it's a record that Jermaine Dupri produced, and of whom I've known a long time...It is basically about a guy making an approach towards a woman on the first date.

[5] Tony Farsides from Music Week felt that the song "is quite downbeat but builds momentum of its own through Dupri's cameo raps and Monica's own impressive vocals.

[7] Writer Troy L. Smith said, "Listening to it now, Monica’s “The First Night” may not feel like a song that topped the charts for a total of five weeks.

"[7] "The First Night" became Monica's sixth top-10 entry and second consecutive number-one hit on the US Billboard Hot 100, reaching the top of the charts in the week of October 3, 1998.

[13] With sales in excess of 1.0 million copies and a 20 week-stay in the top 40 of the Billboard Hot 100, "The First Night" was certified platinum by the Recording Industry Association of America (RIAA).

Throughout the video, there are cuts of her standing up in a white dress and sitting down on a long couch, holding golden opera glasses.