Usher Says Chilli ‘Broke My Heart’ By Turning Down His Proposal Back In The Day: ‘I Went Through A Great Deal Of Pain After That’

Usher, Chilli

Usher Says Chilli ‘Broke My Heart’ By Turning Down His Proposal Back In The Day: ‘I Went Through A Great Deal Of Pain After That’

R&B superstar Usher recently opened up about his past relationship with Chilli.

The latest Super Bowl halftime headliner candidly spoke about the pain their breakup caused and revealed he was even ready to tie the knot.

During a recent interview, Usher Raymond IV, 45, first recalled how he manifested connecting with Rozanda ‘Chilli’ Thomas, 52, as a child. He stated:

“If I am to be honest, I was her No. 1 fan, and she was my superstar…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.’ ”

The singer’s hopes turned into reality years after he relocated to Atlanta to pursue a music career. Not only did he meet the TLC songstress, but the two sparked up a relationship in 2001 when Usher was around  23 and Chilli was around 30. At the time, the pair was one of the hottest couples on the music scene. But things ultimately came to a halt for them in 2004 when they split, which seemingly came after Usher suggested they get married.


Continuing in the interview, the “My Boo” artist revealed he popped the question to Chilli, though she ended up turning down the proposal, leaving him heartbroken. He stated:

“I was a young man, and she had very specific rules that didn’t work for me…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.”

He added:

“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…I hurt her too…[it] broke my heart.” 

As we reported back in June of last year, Chilli also recounted her relationship with Usher. Speaking about their romance, at the time she stated:

“We definitely had some chemistry. But working chemistry does not mean it works in your personal life. If we were working, it was great. But outside of that, we’re so different.”

The Grammy winner also admitted that it was hard for the two to get over each other and shared that their relationship continued on and off for years after their breakup. Usher, however, said he knew their romance would never be the same after the split. He recalled:

“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…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.'”

Now, Usher says the pair have no bad feelings between them and that it’s always “light” whenever they interact. Presently, Chilli seems to have found true happiness with her new partner, “Boy Meets World” star Matthew Lawrence. The two took their romance public back in 2022 and have reportedly been happily in love since.

While Usher recently tied the knot with longtime girlfriend Jennifer Goicoechea following his Super Bowl performance this past Sunday (February 11th). The two began dating back in 2019 and share two young children, daughter Sovereign Bo, 3, and son Sire Castrello, 2.


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Authored by: Kay Johnson