Released on Mya's 1999 album Fear of Flying, 'How You Gonna Tell Me' stands as a defining track of the late 90s R&B and neo-soul movement. The song features a smooth, mid-tempo groove that blends soulful vocals with a polished production style characteristic of the era. Mya delivers a confident and emotive performance that explores themes of relationship dynamics and self-assurance. As a centerpiece of the Fear of Flying album, the track exemplifies the artist's ability to craft intimate yet radio-ready recordings that resonated deeply with audiences. Its enduring appeal lies in its seamless fusion of contemporary hip-hop influences with traditional R&B sensibilities, cementing Mya's status as a leading voice in the genre during the turn of the millennium.