The First Night

Released on July 24, 1998, The First Night arrived as the second single from Monica's sophomore album The Boy Is Mine. The track marked a shift toward a more mature sound for the singer following her massive duet success with Brandy earlier that year. Jermaine Dupri and Tamara Savage wrote the song while Dupri handled production duties, crafting a smooth hip-hop soul groove that balanced rhythmic grit with melodic warmth.

The lyrics explore the specific tension of a first date where sexual desire meets hesitation. This theme resonated deeply with audiences, propelling the song to number one on the US Billboard Hot 100 chart. It became Monica's third consecutive top hit, solidifying her status as a dominant force in late 90s R&B without needing a featured artist.

Hype Williams directed the accompanying music video, which utilized high-contrast lighting and stylish fashion typical of his work during that era. The visual narrative complements the song's story of waiting for the right moment to make a move. The clip has since become a staple of 90s R&B culture, frequently appearing in retrospectives of the genre's golden age. [edit]