Once a union celebrated in the realms of R&B and hip-hop, Usher and Rozonda “Chilli” Thomas found their love story fated to an end. Usher, now 45, delves into the chapters of his past in this week’s cover feature, shedding light on his romantic history and the profound affection he once shared with fellow music luminary Chilli, their relationship spanning from 2001 to 2004.
Embarking on his journey towards stardom, Usher made the pivotal move from Chattanooga, Tennessee to Atlanta, where he unveiled his debut LP at the tender age of 15, followed by his breakout album, My Way, at 18.
The magnetic allure he exuded on those records transcended mere marketing tactics:
“I was always captivating the attention of older women,” he reminisces.
This magnetic pull was palpable when he crossed paths with Chilli in 2001. “To be candid, I was her most ardent admirer, while she epitomized my ideal superstar,” he reflects, alluding to the lyrics of “Superstar” from Confessions, his chart-topping 2004 album that soundtracked the aftermath of their widely chronicled romance.
“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.’ ” But their fan-beloved relationship didn’t work out, and he and Chilli, now 52, split in late 2004.
“I was a young man, and she had very specific rules that didn’t work for me,” he says. “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.”
Even so, he says,
“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.” He admits, “I hurt her too,” but the situation “broke my heart.”
Chilli had previously confided about their dynamic, remarking,
“From the outside, it seemed picture-perfect, but in reality… he felt constrained in our relationship.”
Despite this, she revealed that their connection persisted intermittently for years post-breakup, reigniting during their single phases.
Contrastingly, Usher maintains that their relationship concluded definitively upon their split.
“We maintained an amicable rapport, but I exercised caution,” he explains. “My feelings for her were genuine, and I was unwilling to toy with them. I had given my all, but it seems it fell short of her expectations.”
Both have since found happiness in new relationships: Chilli has found companionship with actor Matthew Lawrence, while Usher recently exchanged vows with his longtime girlfriend, Jenn Goicoechea, in a surprise ceremony following his electrifying Super Bowl halftime performance in Las Vegas this past weekend.
These days, “I’m not hurt over that at all,” he says of him and Chilli not working out.
“We’ve since become cool with each other, celebrate each other and it’s always light when we see each other.”