Usher reveals TLC’s Chilli rejected his proposal before their 2004 breakup

Usher and Rozonda ‘Chilli’ Thomasn dated from 2001 to 2004

Usher has recalled his emotional breakup with TLC’s Chilli.

The Super Bowl halftime show performer, 45, recently opened up about his past relationship with the “No Scrubs” singer, who he dated from 2001 to 2004. In a new cover story with People published this week, Usher revealed that he proposed to Chilli (real name Rozonda Thomas) amid their whirlwind romance, but she rejected his 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,” the “Yeah!” singer told the outlet. “I hurt her too,” he noted, adding that the situation “broke my heart”.

Usher, whose full name is Usher Raymond IV, began dating the TLC member shortly after they met in 2001, when he was 23 and she was 30. The R&B singer admitted Chilli was his “superstar” and he was her “number one fan” when they first crossed paths.

“At the age of eight, I put her poster on my wall and said: ‘Man that girl is so beautiful. One day I’m going to meet her,’” Usher recalled.

Reflecting on their breakup in 2004, he explained that they ultimately split because Chilli wanted to have a “different type of relationship” than the one they already had. “I was a young man, and she had very specific rules that didn’t work for me,” Usher 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 Rozanda "Chilli" Thomas arrive at Mercedes-Benz Fashion Week in September 2002 (Getty Images)

Although Chilli previously claimed that she and Usher were on-and-off for years following their split, he maintained that he closed that chapter once the relationship ended. “We were cool with each other, but I was very careful with that,” he said. “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.’”

Since then, Usher has gone on to marry his longtime girlfriend, Jenn Goicoechea. In fact, the couple tied the knot in Las Vegas just hours after he headlined the Super Bowl halftime show on 11 February. Usher and Goicoechea have been together since 2019 and share two children: daughter Sovereign Bo, three, and son Sire Castrello, two.

He is also a father to two children from his previous relationship with his ex-wife, Tameka Foster. The former couple share sons Usher “Cinco” V, 15, and Naviyd Ely, 14.

Meanwhile, Chilli is currently dating Boy Meets World alum Matthew Lawrence.