Usher reveals he was heartbroken after Chilli turned down his marriage proposal

Usher is opening up about feeling heartbroken following his split from Rozonda ‘Chilli’ Thomas after three years of dating in 2004. 

The 45-year-old rapper, who wed his longtime girlfriend Jennifer Goicoechea in Las Vegas over the weekend, recalled looking at Chilli, now 52, as a “superstar.”

“If I am to be honest, I was her No. 1 fan,” he admitted. “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’.”

While Usher is seven years her junior, he insisted that, at the time, he wanted a more serious relationship, but she didn’t believe that he was “actually in love with her as much as” he said.

“I was a young man, and she had very specific rules that didn’t work for me,” he told People. “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.”

Still, he said wanted to marry her.

“I proposed and she told me no,” he revealed. “I went through a great deal of pain after that, not trusting women or wanting to open up.”

Usher admitted he “hurt her too” but their separation “broke” his heart. 

Chilli previously told the outlet that while their relationship “looked great,” she said “he knew he had to be a certain way with” her, but “couldn’t.” 

Meanwhile, Usher said they “were cool with each other” after their breakup. 

He said: “I was very careful with that. 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’.” 

Like Usher, Chilli has moved on, and is dating actor Matthew Lawrence.