In a recent interview with People magazine however, the artiste revealed that he had in fact proposed to former girlfriend, Chilli, but she refused.

“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 says in the interview, admitting that he too had hurt Chilli, but explaining that the entire situation had broken his heart.
Chilli in a previous interview with PEOPLE said, “It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t.” She noted that their relationship had remained off and on for years following their split and would pick up when they weren’t in other relationships. For Usher however, he says things ended at the time of their breakup. “We were cool with each other, but 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.”

Chilli and Usher are now in a good place following their split many years ago. The 53-year-old TLC singer is dating actor Matthew Lawrence and Usher sealed the deal in surprise nuptials to longtime partner, Jenn Goicoechea. “I’m not hurt over that at all,” said Usher of the situation with Chilli. “We’ve since become cool with each other, celebrate each other and it’s always light when we see each other.”