Usher Reveals That He Proposed to TLC's Chilli and Their Split 'Broke My Heart': 'Really Did Love That Girl' (Exclusive)

The Super Bowl halftime headliner gets candid about his past love life in this week's PEOPLE cover story

Once a match made in R&B and hip-hop heaven, Usher and Rozonda "Chilli" Thomas just weren't meant to be.

Usher, 45, digs deep into his ex-files in this week's PEOPLE cover story, opening up about his past and the deep love he once shared with fellow music star Chilli, whom he dated from 2001 to 2004.

To kick off his dream of becoming a star, Usher moved 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 wasn’t just a marketing creation: “I was always charming the older ladies,” he says.

So it was when he met Chilli, who was seven years his senior, in 2001. “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” on Confessions, his blockbuster 2004 album that was on heavy rotation amid the aftermath of their highly publicized relationship.

“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 53, 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 previously told PEOPLE of their relationship, "It looked great, but in real life ... he knew he had to be a certain way with me and he couldn't." Still she said their relationship remained off-and-on for years following their split and would pick up when they weren't in other relationships.

Usher, however, says that for him, things ended at the time of their breakup. "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 coupled up: Chilli is dating actor Matthew Lawrence, while Usher just tied the knot this past weekend in a surprise wedding to longtime girlfriend Jenn Goicoechea just 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."

For more on Usher's ups and downs in the spotlight and happy life now, pick up this week's issue of PEOPLE, on newsstands everywhere Friday.

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