Inside Chilli From TLC's Star-Studded Relationship History

TLC singer Rozonda "Chilli" Thomas is a force to be reckoned with while performing, but off stage, her personal life is just as fascinating. As a member of one of the bestselling girl groups in American history, Chill has had no shortage of suitors vying for her attention. In the '90s, Chilli and late rocker Prince even went on a movie date to see "Clueless." After her brief stint with the "Purple Rain" legend, several famous men placed their bids to get close to Chilli.

Years later, Rapper Jeezy famously alluded to wanting to pursue Chilli, at least according to the 2010 record "Unforgettable" with Drake.  Speaking of the latter, in 2013, there were talks that Chilli was seeing Drake after he was photographed with her and her son.  That wasn't their first time getting cozy. In 2015, Chilli and the Toronto performer were spotted on a dinner date at a Hollywood restaurant. Although it wasn't a long-term affair, Drake, who also had his share of surprising relationships, and their rumored fling was another noteworthy moment in Chilli's star-studded dating history.

After joining TLC in 1991, Rozonda "Chilli" Thomas caught the attention of Grammy award-winning record producer Dallas Austin. Their relationship nearly got Chilli kicked out of the group. Perri "Pebbles" Reid, TLC's manager, strongly disapproved of the singer dating someone working so closely with the group. She even began auditioning for other vocalists to join the trio, though ultimately, she forgave Chilli, who stayed with Austin for several years. Still, their time together was filled with infidelity on Austin's part, which was detailed in the VH1 TLC biopic, "CrazySexyCool."

Chilli stayed with Austin in part due to an abortion she had early in their relationship. The experience left the entertainer devastated to the point where she was desperate to get pregnant again. After the couple's son, Tron Austin, was born in 1997, Chilli stuck around for about four more years until she found love with fellow singer Usher. However, given that Austin was friends with the "Nice & Slow" performer, his blossoming connection with Chilli caused Austin a great deal of hardship both personally and professionally. This didn't deter his child's mother from falling head over heels for Usher, whom she felt was the love of her life.

When Chilli and Usher began dating, they were undoubtedly couple goals for many. She starred as the leading lady in his 2001 music videos for "U Remind Me" and "U Got It Bad," both of which were from his successful "8701" album. Shortly after, it was revealed that the two were an item, something that greatly affected her ex, Dallas Austin. As Usher's friend, Austin was so devastated over the relationship that he chose to give the record "Cool," which he wrote for TLC, to Gwen Stefani instead. Regardless, Chilli and Usher appeared happier than ever.

When Usher released his "Confessions" album in March 2004, many assumed that the lead single of the same title was about the singer cheating on Chilli. However, Chilli cleared the air, assuring fans that the song was not about them whatsoever. She also defended Usher against infidelity rumors before admitting during VH1's "Behind the Music: Usher" that he did begin dating another woman during a brief breakup. During a chat with Us Weekly in 2013, Chilli shared, "When it was time to make a move, I had to do that. I don't care how much my heart was hurting; sometimes you're just supposed to be with people for a reason, and it's not always a lifetime. Even if you want it to be, it just doesn't work out that way."

In November 2022, Rozonda "Chilli" Thomas again fell hard for actor Matthew Lawrence. Since then, the couple has been going strong, occasionally showing off their love for one another on Instagram. The former "Boy Meets World" cast member has gushed over his new lady, telling Entertainment Tonight in March 2023, "My life is in a complete bloom right now. I get to spend time with an amazing woman like Chilli. I've never gotten to be able to experience that kind of relationship before, so it's quite special. She's a really, really special human being." Chilli is also vocal about her admiration for Lawrence, sharing with People in April 2023, "He's perfect for me." In fact, she says since their romance began they'd never had an argument. While being in an interracial relationship may cause problems for some, the couple does not discuss race, opting to focus on their many other similarities, such as their love for family and the close bond that their mothers have forged with one another.

Even with a few bumps in the road, Chilli has seemingly found her prince charming. Lawrence is even open to having a child with her. Though no baby news has been made public, it's refreshing to see Chilli find love once again.