The 'Confessions' singer ended up being in a long-term relationship with his crush.
Usher made his celebrity crush his boo!
In a new interview with Essence magazine, the 45-year-old revealed the celebrity he had his eyes on when he young.
"My first celebrity crush was Chilli," Usher reveals in the "60 Seconds With" series. "I think I was 11 or 12 something like that."
TLC's Rozonda "Chilli" Thomas and the "Confessions" singer began their relationship in 2001 when he was 23 and she was 30. The pair's high-profile romance lasted until 2004 when they split -- after an engagement.
In February, Usher spoke about their relationship, telling People, "If I am to be honest, I was her No. 1 fan, and she was my superstar," he said.
According to the GRAMMY-winning singer, their relationship ended because she had a stringent set of rules that he couldn't seem to follow. Usher shared that he proposed to the "No Scrubs" singer and she rejected his offer.
"I wanted to marry her," he told the magazine. "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 admits, "I hurt her too," but the situation "broke my heart."
Following his relationship with Chilli, Usher was married to Tameka Foster from 2007-2009. Together, the former couple share sons Usher 'Cinco' Raymond V, 16, and Naviyd, 15. Chilli is currently in a relationship with Matthew Lawrence.
In February, Usher married his longtime love, Jennifer "Jenn" Goicoechea -- with whom he shares his two youngest children, Sovereign, 3, and Sire, 2 -- during a surprise wedding ceremony in Las Vegas following his Super Bowl Halftime Show.
In March, the "You Got It Bad" singer dished to ET about the occasion and shared why he and Mrs. Raymond chose that moment to say "I do."
"It was an incredible moment that we felt was great for us," he told ET. "It was a button at the end of an incredible Las Vegas run. My mother was there, her mother was there, the kids were there, our immediate family was there. Matter of fact, everybody was surprised. I'm like, 'No, no, no, we're having a wedding right now. We're gonna go have Elvis officiate us.'"
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