Usher reveals secret proposal to TLC star Rozanda ‘Chilli’ Thomas

Usher has been making headlines for his surprise wedding to girlfriend longtime girlfriend Jennifer Goicoechea after his stellar Super Bowl performance.

But now the singer, 45, has revealed a secret proposal to one of his past flames.

Speaking to People for his cover story, the Yeah! singer dropped the bombshell that he once proposed to girlfriend Rozonda ‘Chilli’ Thomas from TLC, but was turned down.

“I wanted to marry her. I proposed and she told me no,” he shared.

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“I went through a great deal of pain after that, not trusting women or wanting to open up,” the singer candidly admitted, confessing that Thomas “broke my heart.”

According to the star, Thomas, 52, who was seven years his senior, “didn’t believe that I was actually in love with her as much as I was.”

“I really did love that girl,” Usher told the magazine.

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Discussing their on-off relationship after breaking up, the singer said he “did everything” he thought the TLC star wanted, “but I guess my good wasn’t great enough.'”

Usher dated the R&B singer - his first high profile girlfriend – for three years in the early noughties before calling it quits.

The pair first met in 1993 after they were signed to the same recording label, but didn’t start officially dating until 2001.

The musical couple went their separate ways in 2004, not long after which Usher released his highly successful album Confessions, believed to be about the breakup.

Thomas later refuted claims that the album was inspired by their split, telling US Weekly in 2013 that the pair were still “together when he recorded that album.”

The TLC star told the outlet she would “always love him, forever, because he was my first adult love, a real love.”

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Thomas reflected that “sometimes you’re just supposed to be with people for a reason and it’s not always a lifetime, adding “even if you want it to be, it just doesn’t work out that way.”

Since his romance with Thomas, Usher has been in several other notable relationships over the years.

The Hey Daddy singer was married to fashion designer Tameka Foster for two years from 2007 to 2009, and share two sons Usher ‘Cinco’ V and Naviyd Ely together.

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The R&B legend married again in 2015 to Grace Miguel before sadly calling it quits in 2018.

Usher has been dating his current girlfriend – recently now wife – Jennifer Goicoechea since 2019. The pair share a son and a daughter together.

People confirmed Usher and Goicoechea had secretly gotten hitched in Vegas just hours after his Super Bowl Half Time show.

The singer’s reps told the magazine that the pair had tied the knot on Sunday night at the outdoor wedding chapel Terrace Gazebo surrounded by close family and friends. 

Meanwhile, Thomas has been dating American actor Matthew Lawrence since 2022.