Usher Reveals the Startling Truth About His Relationship With TLC’s Chilli Before ‘Something More Sinister’ Occurred
Megastar Usher Raymond’s relationship with TLC singer Rozonda “Chilli” Thomas was one of the most talked-about romances of the early 2000s, and now, he’s opening up about it in a candid segment for Audible’s Words + Music series “The Last Showman.”
The eight-time Grammy winner reflects on how their love story unfolded during a time when celebrity culture was shifting, offering an intimate look into the relationship that played a pivotal role in both his personal life and his music career.
The spark between Usher, now 46, and Chilli, 53, ignited when he invited her to star in his music video. This professional collaboration quickly evolved into something much deeper, with Chilli appearing in several of her label mate’s hit videos like “U Remind Me,” “U Got It Bad,” and “U Don’t Have to Call.”
“I had my share of flings and wild experiences with women,” Usher admits. “But meeting Rozonda was different. It was the first time I experienced the relentless paparazzi presence outside my home.”
Their relationship, which lasted from 2001 to 2004, marked a turning point in Usher’s public persona. At the time, he was proud of the connection they shared and wanted the world to see their love.
“I was very proud of us, and wanted the world to see the love blossoming between us,” he recalls. However, this decision to go public came with consequences, as the constant media attention took a toll on both of them, ultimately breaking them up.
During Usher’s #SuperBowl #HalftimeShow if he brings out Chilli of TLC to “U Remind Me” & or “U Got It Bad” since she was in the videos, I would flip!
They’re in relationships so I know it won’t happen. But, it’ll be an iconic & nostalgic moment. We still want them to work.. 😅 pic.twitter.com/hRW5psARrH
— Jerome Trammel, M.B.A (@MrJeromeTrammel) February 11, 2024
“People had theories,” he said about the split, adding “Rumors were running fast and furiously,” though neither has shared details of why the relationship faded.
When The Jasmine Brand posted about the new Audible show many of their followers chimed in.
“He talks about Chilli more than his wife,” one person wrote, as another added, “The ONE who got away!!!!”
Someone else said, “He still in love with her.”
There were those that wished he never said her name again.
“He speaks on that relationship too often to be on his 3rd marriage with 5 kids. Move on already they were kids,” one follower wrote.
Another said that journalists are the reasons why he speaks on the “Red Light Special” singer.
“I wish yall would stop asking this married man this question,” one comment read, adding, “It’s old and disrespectful to his wife. And Chilli is also in a relationship. Find something else to talk about.”
Looking back, Usher reflects on how their relationship coincided with the end of an era.
“I didn’t have to deal with strangers offering opinions or criticisms of my life on social media,” he says. “But I knew that would change.”
Though social media didn’t yet dominate the public’s interaction with celebrity relationships, the intense scrutiny they faced paved the way for a more invasive, unforgiving culture.
The breakup was particularly painful for Usher, who once revealed that he had proposed to Chilli, only to be met with rejection.
“I wanted to marry her. I proposed, and she told me no,” Usher told People in 2024. “I went through a great deal of pain after that, not trusting women or wanting to open up.”
Chilli, in her own reflection on the end of their relationship, insists that it was not infidelity, but rather a clash of values that led to their split.
“Working chemistry does not mean it works in your personal life,” she explains. “If we were working, it was great, but outside of that, we’re different.”
She further clarifies that Usher never cheated on her during their time together.
As Usher’s career soared, so did speculation about the connection between his personal life and his groundbreaking album “Confessions.” Fans wondered if the songs reflected his experience with the TLC lead singer.
While the “Waterfalls” chart-topper has dismissed any links, Usher stands by the authenticity of the album’s content.
“There is a great deal of truth in that album,” he affirms.
Looking back, Usher views their relationship as taking place during a transformative moment in celebrity culture.
“We were right at the cusp of seeing celebrity culture shift into something more invasive, more sinister,” he reflects. “Everyone was in search of answers, and we were in the midst of it.”
Now, two decades after the 2004 masterpiece, Usher is reflecting in “The Last Showman” not only on his past relationships but also on his career and the role vulnerability plays in his artistry.
Despite his past stumbles, Usher has found happiness again. He married Jennifer Goicoechea, with whom he shares two children, after his memorable Super Bowl LVIII halftime performance.
Chilli also has found love. She’s in a relationship with Matthew Lawrence and says she no longer has a fear of marriage, believing he might be the one.
