Usher and Chilli were one of the most-loved celebrity couples in the early 2000s, but things unfortunately did not work out between the pair, leading to their split.
In a recent interview with PEOPLE, Usher touched on his relationship with the former TLC member, disclosing that she was even his number-one fan before he became a superstar. The My Way singer also opened up about how genuine his love for the 52-year-old was and how he went through significant pain after she turned down his marriage proposal.
The pair became romantically involved in 2001 before ending their relationship in 2004. “If I am to be honest, I was her No. 1 fan, and she was my superstar,” Usher, 45, said in reference to the No Scrubs singer. “At the age of 8, I put her poster on my wall and said, ‘Man that girl is so beautiful. One day I’m going to meet her.’”
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He then touched on their relationship and what caused their split. “I was a young man, and she had very specific rules that didn’t work for me,” he said. “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.”
He added: “I wanted to marry her. I proposed and she told me no. I went through a great deal of pain after that, not trusting women or wanting to open up.” And though the Confessions singer admitted that he “hurt her too”, his proposal being turned down broke his heart.
In a previous interview with PEOPLE, Chilli, whose real name is Rozonda Ocielian Thomas, similarly reflected on their relationship and split. “It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” she said, adding that they subsequently had an on-again, off-again relationship for years following their breakup.
But Usher said he was cautious about how he dealt with her after their split. “We were cool with each other, but I was very careful with that,” he stated. “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.'”
The former couple are currently thriving in their respective relationships. Chilli and actor Matthew Lawrence are currently dating while Usher married his longtime girlfriend Jenn Goicoechea after taking the stage during the Super Bowl halftime show in Las Vegas.
“I’m not hurt over that at all,” Usher said about his breakup with Chilli. “We’ve since become cool with each other, celebrate each other and it’s always light when we see each other.”
