In a revealing cover story for PEOPLE magazine titled “My True Confessions,” Usher respectfully gets real candid about his past and current love life. While speaking with the mag, the Super Bowl halftime headliner, bares his soul about his past relationship with TLC’s Chilli and the heartbreak that followed their split.

The 45-year-old R&B icon began by talking about his journey to stardom which began when he moved from Chattanooga, Tennessee, to Atlanta, where he released his debut LP at the tender age of 15. His smooth persona, showcased on his hit album “My Way” at 18, wasn’t just a marketing ploy. Usher admits, “I was always charming the older ladies.” It was during this time that he crossed paths with Chilli, seven years his senior, in 2001. Usher confesses, “If I am to be honest, I was her No. 1 fan, and she was my superstar.” Their relationship quickly became fan-beloved, with Usher’s hit album “Confessions” serving as the soundtrack to their highly publicized 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,’” PEOPLE quotes. Ultimately their relationship didn’t work out, and he and Chilli, now 53, split in late 2004. As for the reason, Usher explained, “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.” Furthermore, he admits that he longed for a different kind of relationship where they could be together. Usher’s desire to marry Chilli was met with a heartbreaking rejection. He proposed to her, but she turned him down. 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.”

Moving Forward:

Despite the pain and heartbreak, Usher emphasizes that their relationship ended at the time of their breakup. They managed to maintain a friendly relationship afterward, but Usher was cautious not to rekindle any romantic feelings. He reflects, “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.’”

Happily Coupled Up:

Both Usher and Chilli have found happiness in their respective love lives since their split. Chilli is currently dating actor Matthew Lawrence, while Usher surprised the world with a secret wedding to longtime girlfriend Jenn Goicoechea, just after his show-stopping Super Bowl halftime performance in Las Vegas.

Speaking on that, Usher says these days, “I’m not hurt over that at all. We’ve since become cool with each other, celebrate each other and it’s always light when we see each other.”