Usher was left brokenhearted after Chilli turned down his marriage proposal in the early 2000s.
The recent Super Bowl halftime performer, 45, told People Thursday that he popped the question to the TLC member during their three-year relationship, which lasted from 2001 until 2004.
“If I am to be honest, I was her No. 1 fan, and she was my superstar,” he said of the “No Scrubs” singer, who is seven years his senior.
“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 recalled.
Although Usher’s dream of getting to know Chilli came true, their romance didn’t end with a happily ever after.
“I wanted to marry her. I proposed and she told me no,” he revealed. “I went through a great deal of pain after that, not trusting women or wanting to open up.”
While the “Yeah!” singer said the situation “broke [his] heart,” he admitted that he “hurt her too.”
Usher, who was in his early 20s when he dated Chilli, explained that the “Creep” singer “had very specific rules that didn’t work” for him.
“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.”
Chilli shared similar sentiments during an interview with People in June 2023, claiming their split was largely due to differing values and trust issues.
Although she claimed to have stayed in contact with the “Confessions Part II” crooner up until 2019, Usher — who was married to two different women during that span — made it clear that things were strictly friendly between the two.
“We were cool with each other, but I was very careful with that,” he told People.
“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.’”
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Chilli has since found love with “Boy Meets World” alum Matthew Lawrence, whom she started dating in November 2022.
In fact, an insider told TMZ Thursday that the girl group member is unbothered by Usher’s recent confession and is currently vacationing in Jamaica with her beau.
They noted that the songstress takes marriage “very seriously” and wasn’t going to rush into anything.
Meanwhile, the “Burn” singer secretly married girlfriend Jennifer Goicoechea over Super Bowl LVIII weekend.
Although it’s unclear whether the intimate wedding happened before or after the big game, the couple celebrated their nuptials that night at an intimate afterparty.
The newlyweds wore complementary white Dolce & Gabbana wedding looks at the star-studded event.
While the Grammy winner opted for an asymmetrical suit underneath a massive, white fur coat, Goicoechea looked chic in an off-the-shoulder pant suit.
The twosome was first linked in 2019, one year after his split from ex-wife Grace Harry.
He was also married to Tameka Foster, who was in attendance at Allegiant Stadium Sunday to support her ex, from 2007 to 2009.