Usher is now happily married to his long-term partner, Jennifer Goicoechea; they tied the knot after the R&B star wrapped up his Super Bowl Halftime show performance last Feb. 11.
However, the "Daddy's Home" hitmaker revealed that before he finally found true love with his current wife, there was a time when he was convinced that he was going to marry and live happily with his ex-girlfriend, Rozonda "Chilli" Thomas.
"If I am to be honest, I was her No. 1 fan, and she was my superstar," Usher confessed, referencing his song "Superstar" from his 2004 album "Confessions," which was released around the time after their breakup.
"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 recalled of the TLC member.
Usher Proposed to TLC's Chilli
According to reports, the "Yeah!" singer revealed that his relationship with Chilli came with many rules that "didn't work for [him],' and it might have something to do with their seven-year age gap.
"We were missing each other," he continued. "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."
However, Usher was serious about the "No Scrubs" singer and their relationship--enough to actually propose marriage to her.
"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."
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Usher, TLC's Chilli Move On
The "Waterfalls" hitmaker has since moved on from Usher, and so did he. He was married twice before he got together with Goicoechea in 2019.
Chilli is currently dating "Boy Meets World" star Matthew Lawrence; they began dating in November 2022, reports say.
Although Usher has moved on from that heartbreak, he admitted that it damaged him and affected his future relationships.
"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.'"
According to reports, aside from Goicoechea and Chilli, Usher was linked to Tameka Foster, Grace Harry, and model Naomi Campbell.
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