Usher & Chilli Relationship Timeline

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(Photo by James Devaney/WireImage)

Revisiting the history of one of R&B's “IT” couples.

In the symphony of celebrity romances, few stories resonated like the tale of Usher and Chilli. Neither of the two stars needs any introduction. Usher is essentially R&B royalty, while Chilli rose to fame as one-third of TLC, the best-selling American girl group of all time. Rewind to the early 2000s, a time when the R&B heartthrob and the enchanting TLC star embarked on a journey that would captivate the public's hearts. Their relationship, marked by the highs of red carpet glamor and the lows of heart-wrenching rumors, unfolded against the backdrop of fame's relentless spotlight. Let’s unravel the timeline of Usher and Chilli's R&B love story.

2001: Usher & Chilli Begin Dating

(EXCLUSIVE, Premium Rates Apply) Usher and Chilli of TLC (Photo by James Devaney/WireImage)

The pair first crossed paths in 1993, when both acts were signed under LaFace Records. However, it wasn’t until 2001 before the sparks began to fly. Soon after, Usher and Chili went public with their relationship, confirming the speculations swirling around them. Notably, the couple quickly gained widespread attention. They attended events like the Grammys together, and their chemistry was evident in their red carpet appearances. Fans celebrated the union of two musical powerhouses, creating a buzz around the pair. Although their separate musical ventures already propelled them to great fame, their romantic union made them one of the "it" couples of the early 2000s.

2003-2004: Stormy Clouds

Chilli and Usher during The 45th Annual GRAMMY Awards - BMG After-Party - Arrivals at Gotham Hall in New York City, New York, United States. (Photo by George Pimentel/WireImage)

The first two years were marked by public sightings and public affection. However, the couple faced challenges that tested the strength of their relationship. Speculations about Usher’s fidelity and the pressures of their respective careers began to take a toll. In 2003, the duo decided to part ways, leaving fans heartbroken and curious about the details behind their split. Moreover, the media scrutinized their every move, adding an extra layer of difficulty to the already challenging healing process. 

The couple’s love story bled into Usher’s music. The singer, known for infusing personal experiences into his lyrics, is still widely believed to have expressed his feelings for Chilli in songs like "Superstar," which was part of his Confession album. On the album, Usher admits to several instances of infidelity, feeding the ravenous gossip-mongers.

However, in an interview promoting VH1’s biopic Crazy, Sexy, Cool: The TLC Story with US Weekly, Chilli cleared the air about Usher’s album being about her. “We were together when he recorded that album. 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.”

2019: Chilli Calls It Quits With Usher (For Good This Time) 

Usher and Chilli (Photo by Larry Busacca/WireImage)

After the breakup, both Usher and Chilli took time to reflect on their individual paths. Usher continued his successful music career, while Chilli focused on personal growth and her endeavors outside TLC. The years following their separation saw the former couple pursuing their passions and finding solace in their respective journeys.

The two were on and off for years, and Chilli maintained contact with her ex because she couldn’t find it in her to let him go. She eventually cut off contact with Usher for good in 2019, admitting to People that she wanted 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. I would never want to straddle the fence.”

Conclusion

The relationship between Usher and Chilli showcases the complexities of love in the spotlight. The public's fascination with celebrity relationships, fueled by relentless media coverage, highlights these couples' unique challenges. As we reflect on the love stories of the iconic couple, we are reminded that behind the glamor and fame, celebrities are individuals navigating the intricate dance of love, heartbreak, and self-discovery.

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About The Author
Demilade Phillips has been a Features Writer for HotNewHipHop since 2023. The self-proclaimed music fanatic deals with most things Hip Hop and R&B, while also covering film, television, and the entertainment industry at large. When he’s not working, the International Relations graduate is either binging anime, immersing himself in the underground EDM scene, or crafting up original pieces.