Usher Reveals He Proposed to TLC's Chilli, Says Breakup Broke His Heart

Usher is confessing that his ex, Rozonda "Chilli" Thomas of the supergroup TLC, was a big heartbreak of his life. The two dated from 2001-2004 and reportedly split due to Usher's infidelity. He's since been married three times, recently exchanging vows with his longtime girlfriend, Jennifer Goicoechea, after his record-breaking performance at the 2024 Super Bowl Halftime Show. But Usher and Chilli will always be considered one of R&B's royal couples. In a recent interview with PEOPLE, the "Yeah" singer opened up about how Chilli's rejection was the catalyst for some of his playboy behavior that followed. 

"I was a young man, and she had very specific rules that didn't work for me," he recalls. "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. I hurt her too," but the ordeal "broke my heart." 

Despite their split, Chilli admitted in her own interview with PEOPLE a few years back that they dated on and off for years, with Chilli admitting they didn't stop communicating fully until 2019. Of that, Usher 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.'"

He says long before they met, she was his crush. "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,'" he recalled. Now, he says there's no hard feelings and they both wish each other well.

Chilli is currently dating actor Matthew Lawrence. The two recently celebrated his 44th birthday with a trip to Jamaica. Of Usher's recent admission, Chilli's sources told TMZ that she's unbothered by him bringing things up as she's focused on her romance with Lawrence. The source says Chilli and Lawrence are serious, and the "Waterfalls" singer previously said she is hopeful she and Lawrence will make it down the aisle.