The music icons were an item publicly from 2001-2004. Their love was immortalized in several videos, songs, and appearances. While Usher has been married twice since their split and Chilli has been on a journey to find happiness, the “No Scrubs” hitmaker recently revealed that she and Usher kept in touch all the way up through 2019.
Chilli shocked the world when she appeared at the end of the video for Usher’s single “U Remind Me.” She would appear again in “U Got it Bad” and “U Don’t Have to Call,” with the pair confirming that they were indeed dating in real life.
Both artists had roots in Atlanta and became megastars in the ’90s. By the time they split in 2004, Usher released his album Confessions which many believed to be about his split from Chilli. In real life, it was revealed that much of the songs were actually about Jermaine Dupri’s life.
In the years since Chilli has been notoriously single and picky about the men she dated. While she had been linked to Floyd Mayweather, Marlon Wayans, and Tyrese Gibson, no one knew she and Usher were still secretly hooking up behind the scenes.
During a recent interview, she confirmed that her on-again, off-again love with Usher was a big reason why she was struggling to finally move on.
“We definitely had some chemistry,” she admitted. “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.” Chilli says that in real life, Usher was not able to be the man she needed him to be.
Despite that, they kept revisiting the romance until they finally realized it would not work in 2019. “I love hard; I was like, ‘God, why can’t I get over this?’ He couldn’t either,” she recalls.
Fans in the comments were shocked. “Now see, they were telling us to let it go; meanwhile, they going back and forth up until 2019. 👀 2019 😮” said one person. Chilli is now dating Mathew Lawrence of Boy Meets World fame.