In “How Does It Feel,” Chlöe recruits first-time collaborator Chris Brown to depict the two reminiscing on their broken romances as their exes became unloyal. The single owns a spot on Chlöe’s forthcoming debut album In Pieces. This track also samples Dionne Warwick classic 1973 track “You’re Gonna Need Me.”.

On February 16, 2023, the single was first announced on Chlöe’s Twitter and was faced with backlash for collaborating with Chris Brown, due to his turbulent past. A few days later, Chris voiced his love and support for Chlöe and the track they made together on his Instagram:

24th ❤️ @chloebailey you are a beautiful soul… TAKE OVER THE WORLD SHAWTY and DONT LOOK BACK🙏🏽! YOU ARE A QUEEN! DONT LET NOBODY TELL YOU NO DIFFERENT! You followed your dreams and now the universe is fulfilling that manifestation 🙏🏽❤️

Later that same day, a snippet was first teased in a TikTok video with a behind the scenes taken from the In Pieces' video shoot.