The phrase "How Does It Feel" is the title of a song by American singer D'Angelo, officially titled "Untitled (How Does It Feel)." It was released as part of his second studio album Voodoo in 2000. The song was co-written and produced by D'Angelo and Raphael Saadiq, and it serves as a tribute to the musician Prince, reflecting a vintage sound similar to Prince's early work. Its lyrics are about a man's plea to his lover for intimacy. The song is notable not just for its music but for its music video, which featured D'Angelo appearing mostly nude, enhancing his sex icon image. The video was controversial but widely played, boosting the song's and album's popularity. The song won a Grammy Award for Best Male R&B Vocal Performance in 2001 and is considered one of D'Angelo's signature songs.

So, "How does it feel" in this context is from the song asking a lover how an experience feels emotionally and physically, embedded in a soulful and sensual R&B style.