Chilli’s relationship with Usher was one of the most high-profile relationships in the entertainment industry. The couple started dating in 2001 and quickly became a fan-favorite. They were together for two years before calling it quits in 2003. However, their relationship didn’t end on good terms, as Usher allegedly cheated on Chilli with one of her friends. Despite the drama, Chilli has spoken highly of Usher in interviews and even collaborated with him on his hit song “Love in This Club” years after their breakup.
Chilli’s brief romance with Dallas Austin began in the early 90s when he was producing TLC’s second album, “CrazySexyCool.” The two started dating and even got engaged, but their relationship ended shortly after. Chilli has spoken openly about their breakup, revealing that it was due to Austin cheating on her while she was on tour. Despite the heartbreak, the two were able to maintain a professional relationship and continued to work together on TLC’s music.
In fact, Austin produced many of the group’s biggest hits including “No Scrubs” and “Unpretty.”
Chilli’s rumored fling with Nick Cannon was a hot topic in the media back in 2016. The two were spotted together at a few events and even went on a few dates, sparking rumors of a potential romance. However, both Chilli and Cannon denied that they were dating, insisting that they were just good friends. Despite their denials, fans continued to speculate about their relationship status.
In the end, it seems that the rumors were just that – rumors – and Chilli and Cannon remained friends without any romantic involvement.
One of the most notable relationships in Chilli’s dating history is her long-term relationship with journalist TJ Holmes. The two met in 2006 when Chilli appeared on CNN to promote her reality show, and they hit it off immediately. They began dating soon after, and their relationship lasted for several years, despite the fact that they lived on opposite coasts. In 2013, however, the couple announced their split, with Chilli citing distance as a major factor.
Despite their breakup, both Chilli and TJ have spoken fondly of each other in interviews over the years.
In 2023, it was revealed that Chilli and actor Matthew Lawrence are now dating. Both individuals have gushed over their relationship. Chilli’s bandmate T-Boz says she has never seen Chilli so happy. Matthew Lawrence’s brothers say the same about the actor. When discussing future plans, Matthew has acknowledged he’s interested in building a family with Chilli.