Usher has been loved-up with his girlfriend, Jenn Goicoechea, since 2018 – but before her, he was in a high-profile relationship for years.
The Super Bowl 2024 Halftime Show performer officially dated TLC's Chilli from 2001-2004, although in the years that followed, they would reunite from time to time until she eventually cut all contact with him in 2019.
Chilli has called Usher her first "real love", so why did they break up? Keep reading below to find out…
Who is Chilli?
© Getty ImagesRozonda '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.
© Getty ImagesIn 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 Chilli and Usher date?
© Getty ImagesChilli 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.
© Getty Images"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."
Why did they split?
© Getty ImagesShortly 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."
© Getty ImagesHowever, 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."
© Getty ImagesIn 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.
Who is Chilli dating?
© Getty ImagesChilli 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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