Usher reveals he once proposed to TLC's Chilli: 'She told me no’

We all know Ushe r’s relationship and eventual heartbreaking split from his ex-girlfriend Rozonda “Chilli” Thomas gave us the seminal album that is Confessions , but did you know that at one point during their three years of dating, Usher popped the question?

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Well, according to Usher ’s recent confessions, before calling it quits with the TLC singer in 2004, he proposed, and she said, “no.”

“I was a young man, and she had very specific rules that didn’t work for me,” he told People in a new cover story interview. "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."

“I wanted to marry her," he went on to share of his then relationship. "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.”

“I hurt her too,” he admitted, noting the situation “broke my heart.”

Now, twenty years later, Usher admitted his old wounds have healed. "I'm not hurt over that at all. We've since become cool with each other, celebrate each other, and it's always light when we see each other."

These days, both stars are in happily committed relationships. Chilli has been dating Boy Meets World alum Matthew Lawrence since around November 2022, while Usher recently tied the knot with his longtime girlfriend Jennifer Goicoechea in a surprise Vegas wedding , after his epic Super Bowl Halftime performance .