Usher on TLC's Chilli: "I proposed and she told me no." ....."Broke my heart"

Once hailed as an R&B power couple, Usher and Rozonda "Chilli" Thomas ultimately weren't destined to go the distance.

Usher's journey to stardom began when he relocated from Chattanooga, Tennessee, to Atlanta, where he debuted his first LP at 15 and achieved widespread acclaim with his hit album, My Way, at 18. Reflecting on his early days, Usher admits, "I was always charming the older ladies."

Their love story began in 2001 when he crossed paths with Chilli, who was seven years his senior. Usher candidly reveals, "If I am to be honest, I was her No. 1 fan, and she was my superstar." He fondly recalls admiring her poster at the tender age of 8, dreaming of the day they'd meet. However, despite their fan-beloved status, their relationship faltered, leading to their split in late 2004.

Discussing their breakup, Usher acknowledges the disconnect, revealing, "I was a young man, and she had very specific rules that didn’t work for me." Despite his desire for a deeper commitment, Chilli's reservations left him heartbroken. He confesses, "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."

Chilli has also shared insights into their relationship, remarking, "It looked great, but in real life... he knew he had to be a certain way with me and he couldn't." Despite occasional reunions over the years, Usher maintains that their bond ended with their breakup. He emphasizes his genuine love for her, stating, "I really did love that girl... 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."

Now, both have found happiness with new partners: Chilli is currently dating actor Matthew Lawrence, while Usher recently surprised fans with a wedding to longtime girlfriend Jenn Goicoechea following his show-stopping Super Bowl halftime performance in Las Vegas. Reflecting on his past with Chilli, Usher expresses contentment, saying, "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."