It’s been almost two decades since Usher and Rozonda Thomas, also known as Chilli from TLC, ended their three-year relationship. And now, Usher is opening up about how their breakup affected him and his trust in women.
In an interview with PEOPLE, Usher shared his experience dating Chilli, who is eight years older than him. He admitted to being infatuated with her even as a young boy, with her poster adorning his bedroom wall. Usher said, “I was always charming the older ladies. If I am to be honest, I was her No. 1 fan, and she was my superstar.”
But despite their love for each other, the couple faced challenges. Usher revealed that Chilli had certain rules for him that didn’t work well. “We were missing each other. I really did want to have a different type of relationship where she was there with me, and she couldn’t be. She didn’t believe that I was actually in love with her as much as I was.”
Usher even went as far as proposing to Chilli, but she turned him down. He shared, “I went through a great deal of pain after that, not trusting women or wanting to open up.” This rejection not only hurt Chilli but also left Usher heartbroken.
While Chilli described their relationship as on-and-off for years, Usher clarified that their breakup marked the end for him. He said, “We were cool with each other, but I was very careful with that. I really did love that girl, and I was like, I don’t want to play with you. Like, ‘I can’t give you what I gave you. I did everything that I thought you would’ve wanted me to do, but I guess my good wasn’t great enough.’”
Despite the pain and heartbreak, Usher revealed that he has finally found peace and closure when it comes to his breakup with Chilli. “We’ve since become cool with each other,” he shared. “Celebrate each other, and it’s always light when we see each other.”
After his relationship with Chilli, Usher moved on and had two children with Tameka Foster before their split in 2009. He later married Grace Miguel in 2015, but they divorced in 2018. In October 2019, Usher began a relationship with music executive Jennifer Goicoechea. They welcomed a daughter in September 2020 and a son in September 2021. The couple tied the knot in Las Vegas on Feb. 11 of this year, which was also the day Usher performed at the halftime of Super Bowl LVIII.
Despite the ups and downs in his romantic life, Usher remains grateful for the lessons and growth he has experienced. His journey reminds us that even through heartbreak, healing and love can be found again.
