Usher Reveals He Proposed to TLC’s Chilli & She Rejected Him: ‘Broke My Heart’

The 'Confessions' singer admitted that there were a few reasons that his relationship with the TLC star didn't work out before they broke up in 2004.

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Usher could’ve been married to another musical icon, as he revealed in a new interview. He revealed that he had popped the question to Chilli from TLC (whose real name is Rozonda Thomas) in an interview with People, published on Thursday, February 15. During the pair’s three-year relationship, the Super Bowl performer, 45, admitted that he’d proposed to Chilli, 52, but she rejected him.

Usher explained that when the “No Scrubs” singer turned him down, it “broke [his] heart,” as he recalled the proposal. “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,” he told the outlet. Usher also conceded that he “hurt her too.”

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The “Yeah” singer explained that he had been a fan of Chilli for years, and even as a kid, he’d hoped to eventually meet the R&B star. He called himself her “no. 1 fan,” and called the singer a “superstar.” Despite being a huge fan, Usher said there were aspects of their relationship that they couldn’t agree on. “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.”

Usher and Chilli’s relationship was loved by fans, but it only lasted from 2001 to 2004. Since their split, Usher has been married three times. His first wife was Tameka Foster, and they were together from 2007 to 2009. He then married Grace Miguel in 2015, and they split in 2019. Most recently, Usher reportedly wed his long-term girlfriend Jennifer Goicoechea just days before his Super Bowl performance on Sunday, February 11.

Usher’s most recent wedding was reported just a day after his epic halftime performance! The pair got a marriage license in Clark County, Nevada and after the big game, he was seen with a gold band on his finger while out in Las Vegas, according to People.