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Akil Rucker's Birthday Party - September 17, 2003

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One of the celebrity couples that had the early aughts on tilt was Usher and Chilli.

The two only lasted a few short years, after first hooking up in 2001 and calling it quits in 2004. Twenty years later, it turns out Usher was just as upset about the breakup as his fans.

In speaking to PEOPLE, Usher opened up about his ex-girlfriend, revealing that he didn’t want their relationship to end, and despite being deeply in love with her, she wasn’t buying it.

“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.”

He even explains that he saw a future with Chilli and proposed to her, but despite getting down on a bent knee, she turned him down, which was painful for him. He doesn’t get into detail, but he does admit to hurting her.

“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 said before admitting his own wrongdoings. “I hurt her too,” he added.

Last year, Chilli spoke to PEOPLE about the failed relationship, explaining that there was friction and they couldn’t get on the same page to make the relationship work out.

“It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” she said.

But two decades removed, both have moved on, with Chilli dating actor Matthew Lawrence and Usher getting married to longtime girlfriend Jenn Goicoechea over the weekend.

Usher even adds that he and Chilli have learned to get along and are friendly now that the wounds have healed.

“I’m not hurt over that at all,” he said. “We’ve since become cool with each other, celebrate each other and it’s always light when we see each other.”

See how social media is reacting to Usher speaking out about this ex, Chilli, below.

Usher Says Chilli Broke His Heart After She Declined His Marriage Proposal, Social Media Gives Him The Side Eye  was originally published on