Over the weekend, Super Bowl Halftime Show performerUsher surprised us all when he tied the knot with longtime girlfriend Jennifer Goicoechea. And while the “My Boo” singer has been open about his blossoming relationship with Goicoechea in the past, he recently opened up about another one of his relationships, with TLC’s Chilli.
Talking to People about his and Chilli’s connection, the singer remembered just how enamored he was once of his on-and-off girlfriend before they even met. “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,'” he remembered. A few years later, he did.
Their relationship, however, was rockier than either of them had anticipated. “I was a young man, and she had very specific rules that didn’t work for me,” he told the outlet. “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 detailed. “She didn’t believe that I was actually in love with her as much as I was.”
As a gesture to prove his love, Usher revealed he once got down on one knee. “I wanted to marry her. I proposed and she told me no,” he remembered. “I went through a great deal of pain after that, not trusting women or wanting to open up.”
The pair, which started dating in 2001, split up for good in 2004.
“I hurt her too,” he added, noting that their breakup “broke my heart.”
“I really did love that girl, and I was like, ‘I don’t want to play with you,'” Usher remembered. “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.'”
And while the story of their breakup is beyond heartbreaking, we’re glad each of them moved on and found partners who are their perfect matches. While Usher recently tied the knot with Goicoechea, Chilli has been dating actor Matthew Lawrence for over a year.
Before you go, click here to see all of the 2023 couples we never saw coming.
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