Home • Relationships Usher's Former Flames Usher's Former Flames By Essence · Updated October 30, 2020 01 6982 Usher Greyvest 240×340 Usher and Chilli at Mercedes-Benz Fashion Week in New York City in 2002. Jim Spellman/WireImage.com 02 6992 Usher Costume 240×340 In 2003, Usher celebrated his 25th birthday in costume with then-girlfriend Chilli in West Hollywood, CA. Jean-Paul Aussenard/WireImage.com 03 7002 Usher Whitesuit 240×340 Naomi Campbell accompanied Usher to the MTV Europe Music Awards back in 2004. REUTERS/Dylan Martinez 04 7022 Usher Purplesweater 240×340 Usher and former red-carpet companion and model, Eishia Brightwell, at Russell Simmons’ East Hampton Estate in 2005. Djamilla Rosa Cochran/WireImage.com