Usher Reveals TLC’s Chilli Rejected His Marriage Proposal Before Their 2004 Breakup

In the early 2000s, Usher and Chilli were a popular celebrity couple. However, their relationship did not work out, leading to their breakup.

In a recent interview with PEOPLE, Usher discussed his friendship with the former TLC member, revealing that she was his number one fan before he became a superstar. The My Way singer expressed his real affection for the 52-year-old and the pain he experienced after she declined his marriage proposal.

In 2001, the couple began a romantic relationship, which ended in 2004. Usher, 45, stated, “If I am to be honest, I was her No. 1 fan, and she was my superstar,” referring to the vocalist from No Scrubs. “At the age of eight, I hung her poster on my wall and exclaimed, ‘Man, that girl is so lovely. “One day, I’ll meet her.”

He then discussed their relationship and what prompted their breakup. “I was a young man, and she had very specific rules that didn’t work for me,” he told me. “We missed each other. I genuinely wanted a different form of connection in which she was present with me, but she couldn’t be. She didn’t believe I was as deeply in love with her as I was.

He said, “I wanted to marry her. I proposed, and she said no. I was in a lot of agony following that, not trusting women or wanting to open out. Despite admitting that he “hurt her too,” the Confessions singer’s request was rejected, which crushed his heart.

Chilli, actual name Rozonda Ocielian Thomas, previously spoke with PEOPLE about their romance 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 claimed. They then had an on-again, off-again relationship for years after their breakup.

However, Usher expressed caution in dealing with her after their breakup. “We were cool with each other, but I was very careful with that,” he said. “I truly liked that girl, and I said, ‘I don’t want to play with you. Like, ‘I can’t give you what I gave you. I did all I thought you would have wanted me to do, but I believe my efforts were insufficient.

The former pair is today thriving in their individual relationships. Chilli and actor Matthew Lawrence are currently dating, while Usher married his longtime girlfriend Jenn Goicoechea after performing at the Super Bowl halftime show in Las Vegas.

“I’m not hurt at all,” Usher remarked of 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.”

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