Usher On His Relationship With Chilli: 'Really Did Love That Girl'

"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,” he said. “She didn't believe that I was actually in love with her as much as I was.”

In fact, Usher saw a life with Chilli as his wife.

“I wanted to marry her,” he says. “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.”

Usher admits, “I hurt her too,” adding that the end of their relationship ultimately “broke my heart.”

"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,” he reflects. “I did everything that I thought you would've wanted me to do, but I guess my good wasn't great enough.'"

Fortunately, love made its way back to the R&B singer for a second time. On Feb. 11, the 45-year-old singer surprised fans after marrying his longtime girlfriend, Jenn Goicoechea, following his spectacular Super Bowl halftime performance in Las Vegas. In a previous exclusive with PEOPLE, Usher shared about the spark he has found with his new flame, "I have an amazing partner, a support system."

Today, Usher reminisces on his Y2K-defining relationship with Chilli fondly noting, "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."

Whether in this lifetime or the next, it’s clear that Chilli will always be his “boo.”

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