Usher reveals that he proposed to TLC’s Chilli before their split: 'I wanted to marry her'

“She didn't believe that I was actually in love with her as much as I was."

Usher is getting candid about his heartbreaking split from his ex-girlfriend Rozonda “Chilli” Thomas.

The couple called it quits in 2004 after three years of dating. In the aftermath, Usher dropped his blockbuster album Confessions, which led fans to speculate about the reason behind their breakup — despite Chilli’s insistence that he recorded the songs while they were still together.

Hot off his performance at the 2024 Super Bowl halftime show, the singer has opened up about their split.

“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."

<p>Evan Agostini/ImageDirect</p> Rozanda "Chilli" Thomas and Usher

Evan Agostini/ImageDirect

Rozanda "Chilli" Thomas and Usher

Bu that didn’t deter Usher from popping the question. “I wanted to marry her," he said. "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, but added that the situation “broke my heart.”

Chilli previously told PEOPLE that severing ties with Usher after their breakup was difficult; they were off and on for years.

"I love hard," said the TLC singer in 2023. "I was like, 'God, why can't I get over this?’ He couldn't either."

Usher, however, said he made a concerted effort to maintain boundaries.

"We were cool with each other, but I was very careful with that," he told PEOPLE. "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.'"

<p>Larry Busacca/WireImage</p> Usher and TLC's Chilli

Larry Busacca/WireImage

Usher and TLC's Chilli

Both stars are now happily committed. Chilli is dating Boy Meets World and Mrs. Doubtfire actor Matthew Lawrence, while Usher recently tied the knot with his longtime girlfriend Jennifer Goicoechea in a surprise Vegas wedding.

Twenty years after their separation, Usher says his old wounds have healed. "I'm not hurt over that at all," he said of their relationship. "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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