Usher has a pretty long list of past romances, many of which ended in less than friendly terms.
But although Usher and Chilli haven’t been romantically linked for years, fans are still curious to find out more about what really happened between them.
How Chilli and Usher Met
They first met all the way back in 1993 when Usher signed with LaFace Records, where Chilli was also recording as a member of TLC.
At the time of signing his deal, Usher was just 14 years old, while Chilli was 21.
However, it would be almost ten years later before they would finally get together.
While they were dating, they grew a lot closer in their professional lives, too.
Chilli featured in several of Usher’s music videos in the early 2000s, including You Got It Bad and U Remind Me.
In 2003, the couple made one of their most well-publicized appearances together at the Grammy Awards.
Fans were thrilled to see the glamorous pair together, but this might have marked the beginning of the end for Usher and Chilli.
Chilli and Usher’s Scandalous Rumors
The following year, allegations surrounding their breakup led to public outcry.
The circumstances of their split were the focus of a lot of attention, and some pretty scandalous rumors emerged which would capture the imagination of R&B fans for years.
In 2004, Chilli first hinted that the split might have come about due to infidelity on Usher’s part.
Fans were scandalized to hear her say on The Bert Show that while they were together, Usher committed the so-called ultimate no-no.
The implication seemed pretty obvious to most fans.
Rozonda ‘Chilli’ Thomas’ Damning Remarks
This was made worse when Chilli went on to add that she wouldn’t ever take Usher back.
Fans were stunned by Chilli’s comments, but things only got more serious with her next damning remarks.
Chilli said, “If someone cheat[s] one time, you don’t wait around to see if they’re going to do it again.”
How Usher Responded to Cheating Allegations
Usher then fell under the spotlight of a critical public, but he chose not to respond directly to any of the allegations.
At least, not in interviews.
Instead, Usher went on to release one of the most influential R&B albums in history, which also appeared to serve as his way of dealing with his relationship troubles.
Confessions was released in March 2004.
It was a huge commercial and critical success.
But many fans also thought that Confessions was Usher’s outlet to express feelings of guilt about what happened with Chilli.
In Confessions Part II, Usher alluded to an affair with a mistress which was thought to take inspiration from Usher’s real life.
Usher Raymond Shut Down Infidelity Rumors
It wasn’t long before Usher was facing questions about the reasons behind his breakup.
However, any idea of Usher being unfaithful to Chilli was quickly shut down.
In response to the rumors, Usher said that he loved Chilli, but things just didn’t work out.
He added that “cheating was not what caused the relationship to collide and crash.”
Usher also explained that much of the album’s material was inspired by situations his friends had gone through.
In 2006, producer Jermaine Dupri backed this up by claiming that Usher was inspired by his own affair, in which he cheated on his girlfriend and had a baby with another woman.
Chilli Confronted Usher About Cheating Allegations
It would be a few years before we heard from either Chilli or Usher again on what happened between them.
In 2010, Chilli featured on an episode of VH1’s Behind the Music, in which she touched on her old romance.
She remembered hearing some rumors that Usher had been unfaithful, which she then confronted the singer about.
Chilli Said Usher Admitted Cheating Rumors Were True
And what Chilli claimed happened next threw everything into doubt once again.
She said that Usher admitted that the rumors were true.
She went on to explain what a “fool” she felt she’d been due to everyone else knowing something she didn’t.
However, the story took another twist a few years later.
Rozonda ‘Chilli’ Thomas Retracted Shocking Cheating Claims
In 2013, Chilli made a full retraction of her shocking claims.
She told Us Magazine that Usher never cheated on her and added that he was her first true love.
She even stated that the couple were still together when Usher was making the Confessions album, which seemed to prove that it couldn’t have been about her.
She also backed up Jermaine’s claims that he was the real subject of the songs.
Chilli blamed the timing of their breakup and the album’s release for fuelling the rumors that infidelity had been the cause of their split.
Instead, Chilli only said that they broke up because it was the right time.
Chilli Said ‘There’s No Hard Feelings …’
The TLC star also made it clear that in the years since, she had held no ill will toward her ex.
She said that she didn’t care how much it hurt her to split up because she believed that she was with Usher for a reason and that didn’t have to mean they stayed together forever.
Chilli insisted that these days, “There’s no hard feelings, nothing like that. It’s all good.”
Usher Opened Up About His Romance With Chilli
For his part, Usher has also opened up more in recent years on his history with Chilli.
He reflected on their relationship in an interview with People magazine.
And what he revealed came as a big shock to fans of the former couple.
Regarding the significant age gap between him and Chilli, Usher joked that he was always charming the older ladies.
RELATED: Keyshia Cole’s New Younger Man
Usher Admitted He Was Chilli’s Number 1 Fan
But it seemed like Chilli was a bit more special to the R&B megastar.
He admitted that when they first met, he was Chilli’s number 1 fan.
He described her as his superstar.
Interestingly, another song on Usher’s Confessions album was actually titled Superstar.
Usher even confessed to having a poster of Chilli in his bedroom wall when he was eight years old.
He claimed that when he first saw the poster, he promised himself that he would meet Chilli one day.
Usher Reveals Why His Relationship With Chilli Ended
Later in the interview, Usher finally talked about what caused the relationship to come to an end.
He explained that Chilli had a lot of special rules in a relationship that he was too young to work with.
He also suggested that there was a distance between them, possibly due to their busy schedules, that meant Chii couldn’t be there with Usher the way he wanted her to be.
Usher added that Chilli just didn’t believe that he was as in love with her as he claimed to be.
Usher Said ‘… I Proposed And She Told Me No’
This eventually pushed Usher to make a dramatic gesture that fans were shocked to hear him confess all these years later.
He actually decided to propose to Chilli while they were dating.
He said, “I wanted to marry her. I proposed and she told me no.”
After Chilli rejected his proposal, Usher felt hurt.
In his interview, he said that for a while, he struggled to trust women and didn’t want to open up again.
But that wasn’t the only factor in the relationship’s demise.
Usher Confessed To Hurting Chilli
In a cryptic sidenote, Usher also told People that he hurt Chilli, too.
However, he did not go further into what it was he did to hurt her, although he described the situation between them as heartbreaking.
While it seemed there was a lot of pain for both singers at the time of the breakup, it looks like time has healed their wounds.
These days, they have nothing but good things to say about each other, and both have agreed that infidelity was definitely not what led them to split up.
