Usher Discusses His Touching Proposal to TLC’s Chilli

Usher’s romantic journey takes center stage, complete with twists, turns, and a hint of heartbreak. As he delves into his past romance with TLC’s Chilli, the story unfolds like a chart-topping ballad, revealing layers of passion, regret, and an unspoken yearning for a love that could have been.

Usher invites us into his world of fame, fortune, and emotional complexities through candid revelations and reflections. 

To pursue his dream of becoming a star, Usher relocated from Chattanooga, Tennessee, to Atlanta, where he released his debut LP at 15 and his first hit album, My Way, at 18.

The seductive persona he portrayed on that album was more than just a marketing ploy: “I was always charming the older ladies,” he admits.

In 2001, he met Chilli, seven years his senior. “If I am to be honest, I was her No. 1 fan, and she was my superstar,” he says, nodding to the lyrics of “Superstar” from Confessions, his blockbuster 2004 album that was heavily played in the aftermath of their highly publicised romance.

“When I was eight years old, I hung her poster on my wall and exclaimed, ‘Man, that girl is stunning. “One day, I will meet her.” But their much-loved relationship did not work out, and he and Chilli, now 53, split in late 2004.

Usher and TLC's Chilli
Usher and TLC’s Chilli

“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 previously told PEOPLE about their relationship, “It looked great, but in real life… he knew he had to be a certain way with me, which he couldn’t.”

Nonetheless, she stated that their relationship remained off and on for years after their split and would resume when they were not in other relationships.

However, Usher claims that things ended when they split up. “We were cool with each other, but I was very careful with that,” he says. “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.”

Both are now happily married: Chilli is dating actor Matthew Lawrence, and Usher married longtime girlfriend Jenn Goicoechea in a surprise wedding last weekend, shortly after his show-stopping Super Bowl halftime performance in Las Vegas. 

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.”

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