Usher Admits TLC's Chilli Rejected His Proposal During Early 2000s Romance: 'I Really Did Love That Girl'

Usher was down bad for TLC's Chilli when they dated in the early 2000s.

In a candid new interview, the Super Bowl halftime performer, 45, admitted the girl group member — whose real name is Rozanda Thomas — rejected him when he proposed to her.

"If I am to be honest, I was her No. 1 fan, and she was my superstar," Usher gushed over Chilli, 53, whom he dated from 2001 until 2004. "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.'"

However, the "Yeah!" artist's intense love for the "Scrubs" singer wasn't enough. "I was a young man, and she had very specific rules that didn’t work for me," he recalled

"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 chart-topper was so taken with Chilli that he desperately tried to make things official. "I wanted to marry her. I proposed and she told me no," Usher explained. "I went through a great deal of pain after that, not trusting women or wanting to open up. I hurt her too. It broke my heart."

In the years after their breakup, the "Caught Up" musician still harbored the heartache. "We were cool with each other, but I was very careful with that," he noted.

"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,'" Usher added.

Nonetheless, the Atlanta native learned to let go of the resentment he felt toward his former love. "I'm not hurt over that at all," he explained. "We've since become cool with each other, celebrate each other and it's always light when we see each other."

The "I Miss You So Much" artist opened up about her past relationship with Usher in 2023. "It looked great, but in real life ... he knew he had to be a certain way with me and he couldn't," Chilli said of her ill-fated love with the fellow R&B superstar.

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People conducted the interview with Usher and the 2023 interview with Chilli.