The 'Confessions' singer and TLC star were a couple from 2001 to 2004.
After setting the stage ablaze with his electrifying Super Bowl LVIII Halftime Show performance in Las Vegas, Usher continues to dominate headlines, this time for revelations about his personal life, including his recent marriage to Jennifer Goicoechea and his past proposal to TLC's Rozonda "Chilli" Thomas.
The singer opened up about his romantic journey in an exclusive interview with People.
Usher Chilli were a power couple from 2001 to 2004. Their love story began when Usher, then 23, found himself infatuated with the 30-year-old Chill.
"If I am to be honest, I was her No. 1 fan, and she was my superstar," he says.
Reflecting on their relationship, Usher revealed that their romance faced hurdles due to Chilli's stringent rules, which he struggled to abide by. He longed for a deeper connection where she would be fully present, but her doubts about his love ultimately led to their downfall.
"I was a young man, and she had very specific rules that didn’t work for me," he says. "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."
Chilli turned him down despite his heartfelt proposal, leaving Usher heartbroken and emotionally guarded.
"I wanted to marry her," he says. "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 admits, “I hurt her too,” but the situation “broke my heart."
While their relationship officially ended in 2004, Chilli disclosed in a 2023 interview with People that they continued to navigate an on-and-off dynamic, often rekindling their romance in between other relationships. However, she noted Usher's struggle to reconcile his public image with their private reality.
Contrary to Chilli's perspective, Usher clarified that, for him, their breakup signified closure, though they maintained an amicable rapport. He expressed his enduring love for Chilli and emphasized his reluctance to toy with her emotions or offer anything less than his best.
With their romantic chapter firmly closed, both Usher and Chilli have moved on to new relationships. Usher embarked on matrimony twice before, first with Tameka Foster, with whom he shares two teenage sons, and later with Grace Harry, from whom he eventually parted ways.
This week, Usher exchanged vows for the third time with longtime girlfriend Jennifer Goicoechea, with whom he shares two children. Meanwhile, Chilli has found happiness with Boy Meets World actor Matthew Lawrence since 2022.
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