Usher Reveals TLC’s Chilli Once Turned Down a Marriage Proposal

Usher shared more details about his relationship with TLC’s Chilli during the early aughts, including a marriage proposal that ended in heartbreak for the “Burn” singer.

By Brahmjot Kaur Feb 15, 2024 4:33 PMTags
Watch: Usher Marries Jennifer Goicoechea Ahead of Super Bowl 2024

Usher is revisiting a legendary love. 

The "Superstar" singer reflected on his relationship with Rozonda "Chilli" Thomas back in the early aughts, sharing that at one point he got down on one knee. 

"I wanted to marry her," Usher told People in an interview published Feb. 15. "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."

While he noted that the situation hurt him deeply, he also admitted, "I hurt her too."

The former couple first began dating in 2001 when the "OMG" singer was 23, but the TLC member was actually his celebrity crush for much longer.

"If I am to be honest, I was her No. 1 fan, and she was my superstar," the 45-year-old reflected. "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.'"

Photos from Usher's 2024 Super Bowl Halftime Show

Ultimately, Usher's on-again, off-again romance with the "Creep" ended for good in 2004.

"I was a young man, and she had very specific rules that didn't work for me," he explained. "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."

But despite the hurt at the time, these days, it's all love between Usher and Chilli.

"I'm not hurt over that at all," he admitted. "We've since become cool with each other, celebrate each other and it's always light when we see each other."

Evan Agostini/ImageDirect

In fact, the duo have each found love since then. The "No Scrubs" singer—who shares 25-year-old son, Tron Austin, with her ex Dallas Austin—has been dating Matthew Lawrence for over a year. "We're just very happy and growing in our relationship," Chilli told E! News last March. "I've dated, but this canceled out everything."

As for Usher, he tied the knot with longtime love Jennifer Goicoechea in Las Vegas Feb. 11—the same day the 45-year-old took the stage for the 2024 Super Bowl Halftime Show

And the "Burn" singer—who shares kids Sovereign, 3, and Sire, 2, with Jennifer and is also dad to sons Usher "Cinco" V, 16, and Naviyd, 15, from his past marriage to ex Tameka Foster—couldn't be more excited for the future.

"They both look forward to continuing to raise their children together surrounded by love," his rep told People Feb. 12, "and thank everyone for the well wishes."

Keep reading to see more of Usher's family tree.

Usher "Cinco" Raymond V

Usher became a dad for the first time on Nov. 27, 2007, when he and then-wife Tameka Foster welcomed son Usher Raymond V.

The singer (real name Usher Raymond IV) nicknamed him Cinco as a nod to him being the fifth member of the family to bear the name.

"I have one son, Cinco, who does not like to be called Usher," the singer told Tamron Hall in 2022, "who tries to get away from it."



Naviyd Raymond

Usher and Tameka welcomed Naviyd Raymond on Dec. 10, 2008.

According to the Grammy winner, his second son "really loves entertainment" and is perhaps dad's biggest critic.

"Not only does he watch my show, but he gives me critiques," Usher quipped to Tamron Hall. "He's like, 'You missed this thing. you didn't do this thing.' And I'm like, 'Yeah that's the point. It's not supposed to be the same every night.'"


Tameka Foster

Tameka is Usher's first wife. She worked with the singer as his stylist before their relationship turned romantic in 2005.

The pair tied the knot on Aug. 3, 2007—just months after announcing their engagement—before celebrating their marriage with a larger wedding ceremony on Sept. 1, 2007.

However, their romance fizzled out by June 2009, with Usher filing for divorce in Atlanta. Though the divorce was finalized five months later, Usher and Tameka spent years fighting in court over the custody of their two sons

Ultimately, the R&B icon was awarded primarly custody of Usher V and Naviyd in 2012. 

In recent years, Usher and Tameka appeared to be on good terms. He wished the fashion designer a happy Mother's Day in 2023, writing on Instagram, "Thank you for the gifts you've given. I appreciate you."

Sovereign Raymond

Usher became a girl dad after girlfriend Jennifer Goicoechea gave birth to their first child together—a daughter named Sovereign Raymond—on Sept. 24, 2020.

"Sovereign is such a beautiful word and name to me," he shared of the moniker's meaning in 2021 interview with Extra. "A supreme ruler is obviously the defined name."

And since the little one is the only girl in his brood, Usher quipped at the time, "She's definitely ruling the household."

Sire Raymond

Usher and Jennifer welcomed son Sire Raymond on at 6:45 p.m. on Sept. 29, 2021. At the time, the baby boy arrived weighing 7 pounds, 13 ounces.

"He's different than any of my other kids," Usher told People in 2022. "I've managed to have a little code going with him when I talk to him and how we speak to each other. He makes me mush."

Jennifer Goicoechea

Jennifer was first linked to Usher in October 2019, when she was photographed kissing the "Yeah!" artist backstage at one of his shows. Four months later, the pair stepped out at Vanity Fair's annual Oscars after-party together.

"I have an amazing partner, a support system," Usher said of the music exec in a 2023 interview with People. "We have any amazing dynamic between our relationship where I'm able to be passionate still about what I do and have an incredible partner to work through some of the harder times as a young man dealing with children and dealing with the dynamic of how you communicate with them."

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