Usher tied the knot with Jennifer Goicoechea after performing the ​Halftime show at the 2024 Super Bowl on Sunday, February 11, but she wasn’t the first woman he ever asked to marry him. The “My Boo” singer revealed that he once proposed to Rozonda “Chilli” Thomas from TLC.

“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, 45, told People in an article published on Thursday, February 15.

“I hurt her too,” he continued and added that the situation “broke [his] heart.”

Usher ​dated Chilli, ​52, ​from 2001 to 2004, but the R&B star admitted that he had his eyes set on ​her​ from a much earlier age.

“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 confessed.

While the “Confessions” singer achieved his dream and then some, their relationship ultimately didn’t work out in the long run.

“I was a young man, and she had very specific rules that didn’t work for me,” he told People. “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 Chilli have both moved on from their romance. While Usher recently married Jennifer, ​40, Chilli has been in a relationship with Matthew Lawrence since November 2022. However, the “Yeah” ​singer added that he felt his “good wasn’t great enough” for the “Creep” songstress.

Usher and "Chilli" Thomas of TLC attend the 3rd Annual Black Entertainement Telelvision Awards
Frazer Harrison / Getty Images

“We were cool with each other, but I was very careful with that,” Usher added. “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.'”

Despite everything, the Grammy winner said that he and Chilli have “become cool with each other, celebrate each other and it’s always light when we see each other.”

Chilli has also ​spoken about their relationship. The “No Scrubs” singer said that even though she and Usher officially split in 2004, they would often find their way back to one another and date when they weren’t in other relationships.

“It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” the TLC star told People during a June 2023 interview.