Chilli’s romantic involvement with Usher was among the most widely recognized relationships in the entertainment world. Commencing their relationship in 2001, the couple swiftly gained popularity with fans. Their union endured for a span of two years before coming to an end in 2003.

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Nonetheless, their romantic relationship concluded amidst turbulence, with allegations of Usher’s infidelity involving one of Chilli’s acquaintances. Despite this discord, Chilli has consistently praised Usher in interviews and notably collaborated with him on the hit song “Love in This Club,” several years following their separation.

Chilli’s brief love affair with Dallas Austin commenced in the early 1990s during his production work on TLC’s second album, “CrazySexyCool.” Their romance began to bloom, leading to an engagement, but ultimately, their relationship met an abrupt end. Chilli has candidly discussed the breakup, disclosing that it stemmed from Austin’s infidelity while she was on tour. Remarkably, despite the heartbreak, they managed to maintain a professional partnership, continuing to collaborate on TLC’s music.

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In 2016, Chilli’s alleged involvement with Nick Cannon became a subject of intense media speculation. Their appearances together at various events and a few outings fueled rumors of a budding romance. However, both Chilli and Cannon refuted these claims, maintaining that they were nothing more than close friends. Despite their public denials, fans persisted in speculating about the nature of their relationship.

Ultimately, it appears that the rumors were indeed just that – unsubstantiated rumors. Chilli and Cannon continued to maintain a platonic friendship, with no romantic connection between them.

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One of the most significant relationships in Chilli’s romantic history was her enduring connection with journalist TJ Holmes. Their paths crossed in 2006 when Chilli made an appearance on CNN to promote her reality show, and an instant connection was sparked. Shortly thereafter, they commenced dating, sustaining their relationship for several years, despite the geographical distance that separated them. However, in 2013, the couple made the public announcement of their separation, with Chilli highlighting the distance as a substantial contributing factor.

Remarkably, despite their parting, both Chilli and TJ have expressed warm sentiments about one another in various interviews throughout the years.

In 2023, it was disclosed that Chilli is presently in a relationship with actor Matthew Lawrence. Both individuals have openly shared their affection for one another. Chilli’s bandmate, T-Boz, has noted that Chilli appears to be happier than ever. Similarly, Matthew Lawrence’s brothers have made the same observation about the actor. When discussing their future aspirations, Matthew has openly expressed his interest in starting a family with Chilli.