Usher Opens Up About Painful Split From TLC’s Chilli: “I Really Did Love That Girl”

Usher recently opened up during an exclusive interview with PEOPLE about his unsuccessful relationship with Chilli from 2001 to 2004.

At 18, he released his first hit album, “My Way,” in which he says his seductive persona wasn’t just a marketing ploy.  “I was always charming the older ladies,” he said.

Speaking of Chilli, despite a seven-year age difference, the R&B singer openly acknowledged, “I was her No. 1 fan, and she was my superstar.” This acknowledgment refers to the lyrics of “Superstar” from his 2004 album, “Confessions,” which detailed the aftermath of their highly publicized relationship.

“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.”

He continued, “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.”

However, according to Chilli, “It looked great, but in real life … he knew he had to be a certain way with me, and he couldn’t.”

Chilli said the relationship remained off-and-on for years despite their split, rekindling when they were not involved with other partners.

But for Usher, he said things ended when they broke 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 parties are in new, happy relationships.

Earlier this week, it was announced that Usher and his long-time girlfriend, Jennifer Goicoechea, tied the knot after the 2024 Super Bowl.

Chilli has also been dating actor Matthew Lawrence since November 2022.

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.”