All Of The Men Rozonda ‘Chilli’ Thomas of TLC Has Been Rumored To Date

The women of TLC had almost every man trying to give them a little tender love and care. Rozanda “Chilli” Thomas, dubbed the “Sexy” one out of the CrazySexyCool clique, had (and still has) her share of suitors who would like to “Creep” with the Grammy Award-winning singer. There is public knowledge of her relationships with two celebrities who definitely would fall in the “No Scrub” category. Judging from her long list of requirements for men wanting to date her, this is not far-fetched. But Chilli has been rumored to date a few people you may not have known about.

Chilli and her bandmates came out the gate swinging with their debut album, Ooooooohhh… On the TLC Tip.  During the album’s creation, Chilli and one of the album’s primary producers, Dallas Austin, became romantically involved in a relationship. Their love affair was initially behind their label bosses’ backs until they could not hide it anymore.

Early in their relationship and Chilli’s career, she got pregnant by Dallas Austin. But the couple spent $300 to get an abortion because they thought the pregnancy would hinder or ruin Chilli’s career. Later, she would admit that it was a decision that she regretted, as reported by Amo Mama.  But in 1997, Chilli gave birth to their first and only child, Tron Austin.

Following their relationship, Chilli entered what would become her most high-profile relationship. Rumors began to circulate that the TLC singer and R&B singer Usher were dating after she appeared as the leading lady in multiple of his music videos. Finally, the couple announced that they were indeed a couple in 2001. 

But although fans were rooting for their love to last, their relationship ended in 2003. The widespread speculation was that Usher cheated on Chilli throughout their relationship. Unfortunately, the release of his Diamond-certified album, Confessions, didn’t make the rumors die any quicker. 

However, years later, Chilli would reveal that their relationship simply fizzled out and that Confessions was not about them. In fact, Chilli told Us Weekly that Usher was her first adult love and that he never cheated on her. 

Unbeknownst to many in the general public, Chilli was in a relationship with comedian and actor Marlon Wayans. While they were together, they kept things remarkably mum surrounding their relationship. However, years later, they both would open up about their romance.

Chilli did an interview with Necole Bitchie in 2008, where she gave an account of their chance encounter. After joining TLC, the singer met Marlon Wayans after somewhat manifesting. Chilli described going to the movies while the group was on tour for their debut album and saw Mo’ Money.  

Chilli mentioned how attracted she was to him at the moment, only to go out later and happen across the film’s star. After meeting one another, Chilli says that the two “clicked instantly.” However, according to the singer, Marlon Wayans was “the one that got away.” The Respect star also expressed that Chilli was a “great person in a separate interview.”

Another man that Chilli was linked to romantically was CNN journalist TJ Holmes. The singer spoke with XXL in 2007. She admitted to being in a relationship with Holmes and eluded that it exposed her to new ways of thinking. Chilli said to the publication that her relationship with Holmes was unlike any other that she had before.  

But the flames of their relationship would later fizzle. In a 2012 interview with The Breakfast Club as per The Jasmine Brand, TJ Holmes slyly dodged the host’s question when asked about Chilli. Instead of speaking of the TLC singer, Holmes diverted to the “South American Country.”

Once again, Chilli became a video girl for another male R&B singer. This time, it would be for Tyrese and his single “Nothing On You.” But rumors quickly circulated that the two had begun a relationship on the low.  In Touch Weekly reported an exclusive that they were dating after Chilli “ignored” Tyrese for a long time.

Then in an interview with The Boombox, Gibson played on the rumors that Chilli was “pregnant” but laughed it off and stated that she was just a “good friend” of his. However, he did admit that “things got heated on the set” of his music video.

For a while, Chilli was granted a reality show on VH1 called “What Chilli Wants.” The singer went on a few dates with boxing champion Floyd Mayweather on the show. She details that they have been friends for years that share a “special bond” between them.  

Mayweather took Chilli to a restaurant where he gifted her flatware made of gold to eat from on their first date. But Floyd Mayweather told Chilli that he felt she would be controlling if they dated, and although he admittedly likes her, he didn’t want to “mess the friendship up.” Nevertheless, Chilli and Mayweather did go on a second date where he took her rollerskating. There, he told her that he wanted the best for her.

The year 2016 brought rumors that Chilli and Nick Cannon were an item.  TMZ cameras even caught the “cute couple” (as they referred to them) leaving a restaurant and alleged they were dating. But those would only turn out to be just rumors. Chilli clarified numerous times that they had a “special friendship.” And while speaking with People, Nick Cannon stated that he would be “lucky” to date her but denied they were nothing more than friends.

Comedian Wayne Brady was also rumored to be dating Chilli at one point. After a period in which Twitter went ablaze with the speculations, Brady denied that they were dating and mentioned they were just good friends. During an interview with Arsenio Hall, he called himself one of the “coolest dudes in the world” because of the rumors. Stating that he only dated her for “three hours,” Brady called Chilli his “make-believe, not quite so boo.”

The “Creep” singer also dated actor Brad James briefly, ten years her junior. The two were seen paired up in many pictures on social media, looking quite cozy together. However, they split after a few months together.

Rumors also swirled that Chilli and author and actor Hill Harper had been dating for some time. Pictures of the two also popped up at events like his book signing.  

And finally, Chilli was rumored to date NFL player Larry Johnson in 2009. Multiple blogs spotted them coupled up at various events. However, the singer never confirmed that they were in a relationship. However, in a bombshell tweet dated September 2019, Johnson listed that he slept with Chilli and a few other prominent women.

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