The Super Bowl 2024 Halftime Show performer's childhood dreams came true when the woman whose poster he had on his bedroom walls as a child became his girlfriend.
Usher officially dated TLC's Chilli from 2001-2004 and he even proposed to her before they split, although, in the years that followed, she claimed they reunited from time to time until she eventually cut all contact with him in 2019.
Chilli rejected Usher's marriage proposal, which he said "broke my heart", despite her calling him her first "real love".
So why did they break up? Keep reading below to find out…
Who is Chilli?
Rozonda 'Chilli' Thomas, 52, is a member of the 90s group TLC alongside Tionne 'T-Boz' Watkins and the late Lisa 'Left Eye' Lopes. They were responsible for hits including No Scrubs, Waterfalls, Creep, Unpretty, and more.
Following Lisa's death from a car accident at the age of 30 in 2002, Chilli and T-Boz continued as a duo.
In 2022, the group was inducted into the Black Music & Entertainment Walk of Fame.
Outside of TLC, Chilli is also an actress and appeared on TV shows including The Parkers, That 70s Show, Living Single and Strong Medicine.
She is also a mom to son Tron Austin, 26, whom she shares with her ex, Dallas Austin.
How long did they date?
Chilli and Usher first met in 1993 after he signed to the same record label as her, LaFace Records, but they didn't start a relationship until 2001.
"We definitely had some chemistry," she told People when reflecting on their romance in 2023.
During their relationship, Chilli appeared in Usher's music videos for his singles U Got It Bad, U Remind Me, and U Don't Have to Call. They officially split in 2004 but would continue an on-and-off relationship for years.
"I love hard," she admitted. "I was like, 'God, why can't I get over this?’ He couldn't either."
In 2019, Chilli put an end to their back and forth and cut all contact with Usher "to focus on myself".
"I even stopped dating," she admitted. "Because before that I thought if I met the right guy during that time that I wasn't over [Usher] it wouldn't work. I would never want to straddle the fence."
When did Usher propose to Chilli?
In a recent interview with People, Usher revealed that he popped the question to his girlfriend before their 2004 split, however, she turned him down.
"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 admitted, adding: "I hurt her too," but the situation "broke my heart."
Why did they split?
Shortly after their breakup, Chilli hinted that Usher had been unfaithful after saying he committed the "ultimate no-no".
Speaking to The Bert Show on Atlanta's Q100, she added: "Someone cheat one time, you don't wait around to see if they're going to do it again."
Elaborating on Usher's alleged infidelity during an appearance on VH1's Behind the Music in 2010, Chilli said that she "kept hearing about it, then I went to him, and I asked him and he … admitted it."
She added: "You know I just, I felt like … a fool, I felt like everybody knew something and I didn't, and I'm … just now finding out."
However, over the years, Chilli has stated different reasons for their split. In 2013, she told Us Weekly: "We broke up because I guess it was that time or whatever...he was that real love for me.
"In any relationship, even when it came to my relationship with Usher when it was time to make a move, I had to do that."
She continued: "I don't care how much my heart was hurting, sometimes you're just supposed to be with people for a reason and it's not always a lifetime. Even if you want it to be, it just doesn't work out that way."
In 2023, she alluded to trust issues as the cause behind their breakup. "It looked great, but in real life... he knew he had to be a certain way with me, and he couldn't," she told People.
Chilli added: "Working chemistry does not mean it works in your personal life. If we were working, it was great. But outside of that, we're so different."
Even though they may not be in contact, Chilli said that when it comes to Usher now, she has "no hard feelings" towards him.
Usher said of their breakup: "I was a young man, and she had very specific rules that didn't work for me. We were missing each other."
He added to People: "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."
What has he said about Chilli?
Usher was infatuated with Chilli years before they even met. "If I am to be honest, I was her No. 1 fan, and she was my superstar,” he said. "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.'"
Despite Chilli claiming the pair were on and off for years after their breakup, Usher claimed that wasn't the case. "We were cool with each other, but I was very careful with that," he said.
"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.'"
Who is Chilli dating?
Chilli is now in a serious relationship with Boy Meets World actor Matthew Lawrence, who was previously married to Dancing with the Stars pro, Cheryl Burke.
They were first linked in November 2022 and went Instagram official that New Year's Eve. "I have never experienced anything like this," she told People of their romance.
"He wants to be the best guy he can be and who God wants him to be. God willing, one day we'll get married."
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