"The First Night" is a song recorded by American singer Monica for her second studio album, The Boy Is Mine (1998). It was written by Tamara Savage and Jermaine Dupri, featuring production and additional vocals from the latter. Built around a sample of Diana Ross's 1976 recording "Love Hangover," penned by Marilyn McLeod and Pam Sawyer, who share co-writing credits on the song. The song is about the protagonist practicing abstinence on the night of her first date, despite her conflicting emotions and strong sexual desires.
Following the major commercial chart success of previous single "The Boy Is Mine," a duet with fellow R&B singer Brandy, "The First Night" song was released on July 7, 1998 as the album's second single by Arista Records. Upon its commercial release, it emerged as one of Monica's biggest successes in years, topping both the US Billboard Hot 100 and the component Hot R&B/Hip-Hop Singles & Tracks chart, becoming her first chart solo topper. A remix version with producer Dupri, and rapper Da Brat appeared as a bonus track on Monica's 1998 CD single, "Angel of Mine".
"The First Night" was written by Tamara Savage and record producer Jermaine Dupri, while production was handled by the latter. In the mid-1990s, Savage, a USC alumni and musical performer, signed a development deal with EMI while she was still in college. In 1997, her mentor, Big Jon Platt, then Senior Vice President of Creative at EMI Music Publishing, started setting up collaborations between her and EMI writers such as Soulshock & Karlin and Jermaine Dupri. 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".
In the music video, directed by Joseph Kahn, Monica is seen dancing in a tight, white top and long khaki pants with a crowd of dancers. Throughout the video, there are cuts of Monica standing up in a white dress & sitting down on a long couch holding opera glasses. Other cuts show boys on the couch then girls on the couch & Monica on the couch with her lover. The instrumental break features breakdancing then cuts back to the dance with the crowd. The video ends with Monica rejecting her lover's kiss while they are seated on the couch.