Usher and Chilli‘s romance has continued to interest the public years after their split.

The pair originally met in 1993 but didn’t start dating until nearly a decade later. Throughout their high-profile romance, Usher featured the TLC singer (whose real name is Rozonda Thomas) in several of his music videos.

After three years of dating, Usher and Chilli called it quits in 2004. Usher went on to release the album Confessions, which led many to speculate that the themes of cheating referred to mistakes he make in his relationship with Chilli.

Chilli initially appeared to hint that infidelity played a role in the breakup. She has since clarified that the R&B record was not inspired by her and Usher. (Songwriter Jermaine Dupri later discussed how his personal life was the true inspiration for the songs.)

“We were together when he recorded that album,” she exclusively told Us Weekly in 2013. “All of those songs on Confessions, that was about Jermaine Dupri’s situation. Usher was just singing it. But people kind of bought into it, it was just the timing of our breakup when the album came out.”

Chilli continued, “So people assumed that album was about us, but it was not. And Usher and I weren’t oil and water. We broke up because I guess it was that time or whatever.” She added wistfully: “he was that real love for me.”

In June 2023, Chilli recalled initially staying in touch with Usher over the years, telling People, “I love hard. I was like, ‘God, why can’t I get over this?’ He couldn’t either.”

Chilli cut off contact for good in 2019 to “focus on” herself. “I even stopped dating. Because before that I thought if I met the right guy during that time that I wasn’t over [Usher] it wouldn’t work,” she recalled. “I would never want to straddle the fence.”

Usher ultimately moved on with Tameka Foster, whom he married in 2007. They welcomed two kids together before their split in 2009. Usher was also married to Grace Miguel from 2015 to 2018 before finding love with Jenn Goicoechea. The pair expanded their family with two kids born in 2020 and 2021.

Chilli, meanwhile, welcomed son Tron with Dallas Austin in 1997, before her romance with Usher. She has been dating Matthew Lawrence since November 2022.

Keep scrolling to relive their romance:

1993

The former couple originally met when Usher signed to the same label as Chilli, LaFace Records. They started dating in 2001 after forming a friendship.

2001

During their relationship, Chilli made cameos in Usher’s music videos including “U remind me” and “U got it bad.”

2003

Chilli and Usher attended the Grammys shortly before their split.

2004

The TLC member alluded that cheating played a role in their breakup when she said on The Bert Show on Atlanta’s Q100 that Usher committed the “ultimate no-no” and that she would “never take him back.” Chilli also noted that if “someone cheat one time, you don’t wait around to see if they’re going to do it again.”

2010

During an episode of VH1’s “Behind the Music,” Chilli recalled “hearing” rumors of infidelity that she told Usher about. “He admitted it. 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,” she claimed at the time.

2013

Chilli subsequently clarified that Usher never cheated on her, telling Us she would “always love” her ex.

“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 said. “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.”

Chilli, who called Usher her first “real love,” said they remained on good terms. “But I’ll always love him, forever, because he was my first adult love, a real love,” she added. “But we’re cool, we’re really cool. There’s no hard feelings, nothing like that. It’s all good.”

2023

During a game of Spilling the E-Tea with Tionne “T-Boz” Watkins, Chilli recalled how she saw Usher in a few movies before they met.

“[I] always thought he was so cute. Like always,” she shared. “And then when I saw him in person, I was like, ‘Oh, OK.’ And you know how I am. So, long story short, once we started talking on the phone and getting to know each other, [we] obviously [have] so much in common.”

She continued: “And it was just a lot of things that we would talk about… And he is a phenomenal man. I just saw it right away, and I was just like, ‘Wow.'”

2023

Chilli opened up about her past connection with Usher, telling People, “We definitely had some chemistry. But 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.”

The musician said differing values and trust issues led to them parting ways.

“It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” she added. “I have no hard feelings.”

2024

During an interview in February 2024, Usher candidly reflected on his romance with Chilli, telling People, “If I am to be honest, I was her No. 1 fan, and she was my superstar. 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.’”

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Usher hinted that distance led to their split. “I was a young man, and she had very specific rules that didn’t work for me,” he continued. “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.”

According to Usher, he proposed to her shortly before their breakup, adding, “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 concluded: “We were cool with each other [after the split], but I was very careful with that. 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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