Usher says he deeply loved singer Rozonda “Chilli” Thomas from TLC, and the breakup was devastating. Usher had the biggest Super Bowl Half Time Show over the past weekend and is likely to rake in over $100 million in royalties, deals, and endorsements.
The R&B artist also celebrates his marriage to long-time girlfriend Jennifer Goicoechea days after his Super Bowl performance. While at the Super Bowl, People interviewed the R&B veteran, who revealed for the first time that he had proposed to Chilli, whom he dated from 2001-2004.
The Tennesse-born artist, 45, revealed that he moved to Atlanta at age 15 to release his debut LP and later his debut album, My Way. Throughout his dating life, he always preferred older women (Chilli was seven years older than him when they began dating).
According to Usher, he grew up seeing Chilli on TV and in magazines and kept a poster of her, always wishing that he would meet her one day.
“If I am to be honest, I was her No. 1 fan, and she was my superstar… 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 said, hinting that the song “Superstar” on his ‘Confessions’ was about Chilli.
The two, however, dated for three years before splitting in 2004. Usher explained why the breakup happened and shared that it was devastating for him.
“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. She didn’t believe that I was actually in love with her as much as I was,” Usher said.
The “U Remind Me” singer added, “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 also said he hurt Chilli, and the end of the relationship “broke my heart.”
Usher has never spoken about the relationship with Chilli, but she previously told PEOPLE that the singer couldn’t meet her standards.
“It looked great, but in real life … he knew he had to be a certain way with me, and he couldn’t.”
In the past, Chilli claimed that she and Usher had an on-and-off relationship for years after the breakup, something he said he was very wary of because of his feelings for her.
“I was very careful with that. 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,” he said.
On a lighter note, Usher says he and Chilli are at a great place and no longer heartbroken. As for Chilli, she is currently dating actor Matthew Lawrence and seemed happy at their recent baecation outing in Jamaica for his birthday.
