Usher Says He Was 'Heartbroken' When Chilli Did Not Accept His Marriage Proposal
Usher recently shed light on his new marriage to Jennifer Goicoechea and the heartbreak from a declined proposal to his ex-girlfriend Chilli.
In an interview with PEOPLE, the "Confessions" singer revealed how he "wanted to marry" the TLC singer while they dated from 2001 to 2004.
"I was a young man, and she had very specific rules that didn't work for me," Usher, 45, said. "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."
Despite Usher's attempt to overcome her distrust in his love, he bravely proposed to Chilli, born Rozanda Thomas.
"I wanted to marry her," he said. "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."
While Usher and Chilli, 52, never rekindled a serious romance, Chilli revealed to the same outlet in 2023 that their relationship remained on and off after 2004. Their connections occurred during periods when they were not involved with other partners. Chilli expressed that Usher recognized the need to adhere to specific behaviors with her, but unfortunately, he felt he "couldn't" meet those expectations.
The Super Bowl LVIII halftime performer maintains that it was a definitive end for him after the initial breakup, although he emphasizes that they remained on amicable terms, describing their post-breakup relationship as "cool."
"We were cool with each other, but I was very careful with that," he said. "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.' "
Two decades after their 2004 split, both Usher and Chilli have ventured into new romantic chapters.
Usher married Tameka Foster and became a father to two now-teenage sons. After divorcing Tameka, he entered a union with Grace Harry, whom he divorced in 2018.
The "Coming Home" crooner jumped the broom for the third time with Jennifer Goicoechea. The couple, who has reportedly been dating since 2018, now share two children.
