Rozonda ‘Chilli’ Thomas’ Boyfriend: Her Romances With Matthew Lawrence, Usher & More

Rozonda “Chilli” Thomas is a force to be reckoned with. As 1/3 of the 90s sensation TLC, alongside Lisa “Left Eye” Lopes and Tionne “T-Boz” Watkins, she rose to fame with hits like “Waterfalls,” “No Scrubs,” and “Creep.” At the height of their fame, the talented trio garnered an American Music Award, multiple Grammys, and a slew of MTV Video Music Awards. Their widely publicized bankruptcy, and Lisa’s tragic death in a car crash on April 25, 2002, presented challenges and grief for Chilli, but she went on to release a couple of solo singles and even appeared in the music video for Tyrese‘s hit “Nothing On You.”

She also starred in two seasons of a VH1 reality series based on her life called What Chilli Wants. Behind the scenes — and sometimes even in full public view — she also had a series of high-profile relationships with famous men. In fact, she’s currently dating actor Matthew Lawrence.  Read on to find out about all of Rozanda ‘Chilli’ Thomas’ most serious romantic relationships.

Dallas Austin

According to The US Sun, Chilli dated TLC producer Dallas Austin throughout most of the 1990s — and he produced some of the group’s most memorable hits. During an episode of her reality series, she opened up about an abortion she had while with Dallas. She also admitted to deeply regretting the decision, and getting pregnant again with Dallas. They ended up  having a son together.

“I was 20 and my career hadn’t really started, [and I got pregnant],” she said during the show, per Buzzfeed. “How do I do all that? How do I be a mommy? [The abortion] messed me up — it broke my spirit. I felt like I became not my strong self anymore. I felt like I gave in and broke [down] to what someone else wanted. I cried almost every day for nine years. And then I was caught up — I had to have a baby. I had to fix it, and the only way I could fix it was with him [Dallas]. I could only have this baby with him because the baby I didn’t have was with him. As time went on, I was able to break away from the relationship because I knew that he was always being true to himself — I was not. I was compromising who I was as a person to please this person, and I think so many women do that.”

The duo welcomed their son Tron Austin on June 2, 1997. Not long afterwards, they went their separate ways.

Usher

R&B star Usher was Chilli’s next serious relationship. Both were members of the LaFace Record Group, and the romance was natural. They began dating in 2001, and in the subsequent two years, she appeared in several of his iconic music videos, including U Don’t Have to Call, U Remind Me, and U Got It Bad.

They split in 2003, but she’s spoken out multiple times about how hard it was to get him out of her system, even admitted they were still in contact when he got married to now ex-wife Tameka Foster. “I love hard,” she told PEOPLE in June of 2023. “I was like, ‘God, why can’t I get over this? He couldn’t either.”

After it was over, she admitted, “I even stopped dating. Because before that I thought if I met the right guy during that time that I wasn’t over [Usher] it wouldn’t work. I would never want to straddle the fence.” She also revealed that they had “working chemistry.” “We definitely had some chemistry,” she explained. “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.”

In a 2013 interview, she recalled their breakup as well. “We broke up because I guess it was that time or whatever…he was that real love for me,” she confessed to Us Weekly at the time. “In any relationship, even when it came to my relationship with Usher, 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.”

Nick Cannon

Unconfirmed reports emerged in July of 2016 that Chilli was “hanging out romantically” with serial dad Nick Cannon. “Nick and Chilli [have] been hanging out on the low, ” an insider reportedly told E! News. “[They’ve] been friends for some time and just recently this summer they have been hanging out romantically.” The source also said that “Chilli is a very mature woman that’s been around the music industry for some time and gets it,” and added the tidbit that “Nick has always had a crush on her growing up. He thinks she is beautiful.”

“They are not an exclusive couple at this time just casually hanging out and seeing where things go,” the source said. Neither Chilli nor Nick have ever addressed the dating rumors.

Matthew Lawrence

Sometime in November of 2022, the TLC singer began dating Dancing with the Stars pro Cheryl Burke’s ex-husband, Matthew Lawrence. By January of 2023, Chilli’s rep had confirmed to TMZ that the couple are in an “exclusive relationship.” They made the relationship Instagram official by dancing in their pajamas via social media just before the new year. But months before that, they were also spotted vacationing together in Hawaii in August of 2022.

In May of 2023, she gushed about the fact that she hadn’t had a single fight with the Boy Meets World actor during their relationship. “I never thought the name ‘Matthew’ would make me blush so much,” the singer told PEOPLE. “I always thought he was cute.” She  then added, “To this day we have not had one argument. I’m like ‘Matthew, it’s gonna happen one day, cause we’re going to be together forever.'”

Matthew seems to feel the same way. “My life is in complete bloom right now,” the TV star told ET  back in March. “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. She’s really, really special.”

Though Cheryl seemed taken aback by Chilli and Matthew’s relationship, it didn’t emerge until nearly a year after they announced their split in February of 2022. Meanwhile, the TLC star has support from another of the most important men in her life — her son, Tron. “I just like seeing her happy, you know?” he told People during an April 2023 interview. “I wish them all the best and I think he’s a great guy.”

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