Fresh off a Las Vegas wedding to his longtime girlfriend, Jenn Goicoechea, over Super Bowl Weekend, Usher is opening up about one of his first true loves in a new People magazine cover story. The singer, 45, spoke to the magazine about his intense romance with TLC’s Rozonda “Chilli” Thomas, whom the “Yeah!” singer met when he moved to Atlanta from his home in Chattanooga, TN as a teenager.
Describing himself as someone who “was always charming the older ladies,” Usher said he was smitten when he met Chilli, now 53, who was seven years older than him when they began dating in 2001. “If I am to be honest, I was her No. 1 fan, and she was my superstar,” he said, adding that he had Chilli’s poster on the wall of his childhood bedroom when he was eight-years-old.
“[I] said, ‘Man that girl is so beautiful. One day I’m going to meet her,’” he recalled saying at the time. And though meeting the woman of his dreams and beginning a relationship with her was magical, Usher said the affair ultimately fizzled because of differing priorities. “I was a young man, and she had very specific rules that didn’t work for me,” he told People of the singer who starred in the videos for Usher’s hits “U Remind Me,” “U Got it Bad” and “U Don’t Have to Call.”
“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,” said Usher, who wowed the crowd at Allegiant Stadium in Vegas during Sunday’s Super Bowl LVIII halftime show. “She didn’t believe that I was actually in love with her as much as I was.”
Despite the difficulties, Usher said his plan to marry Chilli went sideways. “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,” Usher said. “I hurt her too,” he added, noting that the split also “broke my heart.”
Usher, now married for a third time, and Chilli — who began dating actor Matthew Lawrence in 2022 — reportedly remained friendly after their split; Chilli previously told People that they were on-and-off for years after the break-up, reconnecting when they weren’t dating other people. But Usher told the mag that when it ended, he was done for good.
“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.’” But, he noted, these days the two are “cool with each other” and it’s “always light” when they see each other.
Usher dropped his new album, Coming Home, last week. The 20-track collection boasts guest spots from BTS’ Jung Kook, Burna Boy, H.E.R. and more, and is expected to compete with Kanye West’s Vultures for the top spot on the Billboard 200 next week.