Decoding Chilli and Usher's Relationship: A Rollercoaster of Love

Alizabeth Swain - Author

Feb. 19 2024, Published 9:35 a.m. ET

Chilli and Usher relationship timeline
Source: Getty Images

Chilli and Usher — the iconic R&B king and American girl group icon, created a celebrity romance that deeply resonated with the public. After all, what isn't there to love about such a captivating celebrity romance?

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Chilli and Usher's relationship timeline is a captivating journey that interweaves love, music, and fame. Let's take a trip back in time to 2001 to see the first sparks ignite between one of the hottest "It" couples of all time.

The early days of Chilli and Usher's love.

usher and chilli relationship timeline
Source: Getty Images

The story of how Usher and Chilli first crossed paths is a testament to their shared passion for music and the vibrant R&B scene of the early 2000s. According to US Magazine, Usher and Chilli first met in 1993 and didn't start dating until 10 years later. But, the lack of relationship status didn't stop Usher from featuring the TLC star in some of his music videos.

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Shortly after rumors of their relationship began to circulate, Usher and Chilli confirmed that they were indeed a couple in 2001. Fans were thrilled about this love match between two titans of the music industry, which only intensified the buzz surrounding them.

While both Usher and Chilli had already achieved considerable fame through their individual music careers, their romantic alliance elevated their status, making them one of the most iconic couples of the early 2000s.

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The peak of their love was in 2004.

Usher's prominence in the music industry soared to new heights in 2004, largely thanks to his successful album "Confessions." Meanwhile, Chilli continued to establish herself as a prominent figure in the R&B scene.

Together, they became one of the most iconic couples in the music industry, their union further magnifying their individual fame.

Their romantic relationship added a layer of intrigue to their public personas, keeping them in the limelight and capturing their fans' attention.

The short-lived romance and final split between Usher and Chilli.

relationship timeline between chilli and usher
Source: Getty Images

After three years of being together, Chilli and Usher decided to part ways. Chili and Usher began dating in 2001 and called it quits three years later. That same year, Usher released his critically acclaimed album “Confessions,” which many fans believed to be about his infidelity during his romance with Chilli.

However, in an interview with US Weekly, Chilli revealed that Usher didn't cheat on her. Ultimately, Chilli says she broke off their relationship to "focus" on herself.

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In 2024, Usher revealed that he proposed to Chili before their split, telling People, "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 admits, “I hurt her too,” but the situation “broke my heart.”

Post-breakup, Usher and Chilli each embarked on personal journeys of self-discovery. Usher sustained his thriving music career, while Chilli turned her attention towards personal development and pursuits beyond her commitments with TLC.

The period following their split witnessed both individuals immersing themselves in their respective passions, finding comfort and growth in their paths.

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Their relationship experienced several ebbs and flows over the years, with Chilli maintaining a connection with her former beau, unable to entirely sever ties. However, in 2019, she decided to cease all contact with Usher.

Chilli mentioned in an interview with People that she cut Usher off because "any potential relationship wouldn't stand a chance. I didn't want to be caught in a situation of divided loyalties."

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