Usher Reflects On 2004 Split From Chilli Of TLC: “I Proposed And She Told Me No”

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Usher and TLC songstress Chilli famously dated in the early 2000s, with their relationship coming to an end in late 2004, not long after the release of the crooner’s most acclaimed album, Confessions.

Days after tying the knot in Las Vegas, Peoples latest cover star reflected on his time with the singer born Rozonda Thomas, saying he was a fan long before he met the beauty who’s seven years his senior.

“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 admitted. “If I am to be honest, I was her No. 1 fan, and she was my superstar,” he added, referencing lyrics from fan favorite track, “Superstar.”

Usher and Chilli of TLC during The 45th Annual GRAMMY Awards – Arrivals by Gregory Pace at Madison Square Garden in New York, NY, United States. (Photo by Gregory Pace/FilmMagic)
Usher and Chilli of TLC during The 45th Annual GRAMMY Awards – Arrivals by Gregory Pace at Madison Square Garden in New York, NY, United States. (Photo by Gregory Pace/FilmMagic)

Unfortunately, things came to an end due to his own “young” ways and “rules” that Chilli attempted to put in place.

“I was a young man, and she had very specific rules that didn’t work for me. 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,” he revealed, adding, “She didn’t believe that I was actually in love with her as much as I was.”

The R&B star went on to share that he asked for the “No Scrubs” singer’s hand in marriage, but was turned down, resulting in future problems with the women in his life. “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.”

Usher and Chilli (Photo by Larry Busacca/WireImage)
Usher and Chilli (Photo by Larry Busacca/WireImage)

While he was also able to admit, “I hurt her too,” he adds that the situation, “broke my heart.”

Usher has since married and split from Tameka Foster, with whom he shares sons Usher V, 16, and Naviyd, 15. In 2015, Usher quietly married manager Grace Miguel, but the pair split three years later.

Usher’s most recent marriage to Jennifer Goicoechea took place in Las Vegas shortly after his epic Halftime performance. Goicoechea is the mother of his two youngest children, Sovereign Bo and Sire Castrello.

As for Chilli, the stunner has been happily dating actor Matthew Lawrence for a year, as the pair confirmed their relationship in January 2023. The Boy Meets World actor’s birthday, coincidentally, also fell on the day of the Super Bowl, with Chilli sharing a snap of them together as Ursher killed it onstage, miles away.

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