Days after lighting up Vegas with his Super Bowl performance, Usher is still making headlines. But the news has taken a nose dive into this man’s personal life, including Usher’s new marriage to Jennifer and his failed proposal to Chilli.
Raymond revealed the past love life blow while speaking with PEOPLE for his cover story. The ‘Confessions’ singer and TLC star were an early “IT” couple from 2001 to 2004. When they met, Usher was reportedly 23 and the “No. 1 fan” of the 30-year-old at the time. They’re seven years apart in age.
“I was a young man, and she had very specific rules that didn’t work for me,” Usher 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 Says He Proposed To Chilli & She Shut Him Down
Despite her distrust in his love, Usher says he proposed to Chilli. Unfortunately, she rejected the proposal, leading to the end of their relationship. He admits that he caused her “hurt” as well, but the rejection “broke [his] heart” and caused him to become emotionally closed off.
“I wanted to marry her. I proposed and she told me no. I went through a great deal of pain after that.”
Though they never got serious again, Chilli told the same outlet in 2023 that their relationship was on and off after 2004. They’d linked when they weren’t in other relationships. However, she says Usher knew he “had to be a certain way” with her and “couldn’t.”
On the other hand, Usher says it was a wrap for him following the initial breakup but that they were “cool.”
“We were cool with each other, but I was very careful with that. 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.'”
With the 2004 split 20 years behind them, Usher and Chilli have moved on romantically.
Usher went on to marry Tameka Foster and welcomed two sons who are now teenagers. He wed Grace Harry a few years after divorcing Tameka, but they later divorced as well.
Earlier this week, Usher tied the knot for the third time with long-time friend Jennifer Goicoechea. The pair reportedly began dating in 2018 and share two children.
Meanwhile, Chilli has reportedly been dating ‘Boy Meets World’ actor Matthew Lawrence since 2022.
