Rozonda “Chilli” Thomas is beautiful, flaunts a perfect physique, and has a successful career as a member of TLC. She’s the total package but has struggled with finding and maintaining true love.
Here’s the sad truth about Chilli’s dating history.
The one who got away
In 1991, Chilli went from being a backup dancer to joining TLC. In 1992, the group went on its first tour with MC Hammer. During some downtime, they went to the movies and watched the film Mo’ Money. That’s when she caught her first glimpse of Marlon Wayans who played the character Seymour.
In an interview with NecoleBitchie, Chilli said she thought he was so cute. After the movies, they all went out. She ended up running into Marlon that night and they clicked instantly. Their relationship was brief, and Chilli referred to him as “the one who got away.” She added that if she had to look back at her previous relationships and determine who really loved and adored her the most, it would be Marlon.
A regretful decision
As TLC began working on their debut album Ooooooohhh… On the TLC Tip, Chilli hooked up with producer Dallas Austin. Dallas told VladTV they kept things on the low because Perri “Pebbles” Reid, who was TLC’s manager, didn’t approve of the girls being groupies and dating producers. They hid their relationship for a while, and the only people who knew about their romance were fellow TLC members T-Boz and Left Eye. But the secret soon came out when Chilli discovered she was pregnant at the age of 20.
According to Dallas, when Pebbles found out, she kicked Chilli out of the group and started auditioning for her replacement. Pebbles gave a different story to Wendy Wiliams. She said T-Boz and Left Eye were the ones who gave Chilli the boot because they felt her relationship with Dallas was a conflict of interest.
Either way, Chilli was young and scared, and with her career on the line, she decided to terminate the pregnancy. In an unaired scene from the TLC biopic, Chilli admitted Dallas gave her $300 to terminate her pregnancy. Years later while chatting with VH1, Chilli called it one of her “biggest mistakes.” She said, “It messed me up. It broke my spirit.”
Pebbles’ plan to replace Chilli fell through, and she was able to work her way back into the group. She and Dallas continued with their relationship, but there were rumors that Chilli was having an affair with Pebbles’ then-husband, LaFace Records co-founder, L.A. Reid. Both Chilli and L.A. denied the allegation.
Making things right
Chilli tried to move on after ending her pregnancy, but she could never get over what she had done. She told VH1 that for the next few years, she cried every day and became fixated on making things right. She was determined to get pregnant again and the baby had to be by Dallas since he was the father of the child she didn’t have. Dallas was down, and Chilli gave birth to their son Tron Austin in June 1997. They were happy to be parents, but their relationship came to an end sometime around 1999.
Working with an ex
Chilli later told VH1 she had to break away from the relationship because Dallas was always being true to himself, but she was compromising herself to please him. TLC continued their professional relationship with him, although things were sometimes awkward in the studio.
Dallas and Chilli both moved on, and Dallas told Billboard he wrote a song entitled “Cool” after their relationship ended. The song includes lyrics like, “It’s good to see you now with someone else / And it’s such a miracle that you and me are still good friends / After all that we’ve been through / I know we’re cool.”
When it came time to record the track, Dallas changed his mind and didn’t want to give the song to TLC anymore. He said, “I was so aggravated being in the sessions. It was very obvious who it was about and what it was, and it was hard.”
He decided to take the song away from TLC, which angered the group. Dallas eventually gave the song to Gwen Stefani who included it on her debut solo album Love. Angel. Music. Baby.
The ultimate no-no
In 2001, the world was shook when Chilli and R&B heartthrob Usher started dating. Chilli went on to be the leading lady in his music videos for “U Remind Me” and “U Got it Bad.”
Seeing the chemistry they had with each other made the world believe they were a perfect couple. They also appeared together at various red carpet events as Usher promoted his 2001 album 8701. They looked like they were destined to live happily ever after, but the good times didn’t last long.
Usher went back into the studio to put the finishing touches on his album entitled Confessions. He put it all on the line, from songs about cheating and getting other girls pregnant. When the album was released in March 2004, everyone just knew Usher’s infidelity played a role in their turbulent relationship.
While promoting the album on MTV, he addressed the rumors about the status of what many assumed to be an on-again-off-again relationship. He said, “Yeah, I’m single. We’re still friends. It’s just something that happens in life.”
Chilli wasn’t having that mess. She appeared on the radio program entitled The Bert Show in 2004 and said, “Usher did the ultimate no-no to me. I will never be with him again, and that is that.” The final dagger was when she added, “He is so not-cute to me. I don’t ever want to see him again.”
The truth about ‘Confessions’
Once again, everyone assumed cheating was the cause of their breakup. And Usher appeared to be fine with being labeled a cheater because it played into the theme of his album. The publicity certainly helped, and the album earned him three Grammy awards.
In reality, Confessions wasn’t even about Chilli and Usher’s relationship. Chilli told US Weekly the songs were about rapper and producer Jermaine Dupri’s personal experiences. She said, “Usher was just singing it. But people kind of bought into it.”
As far as the end of their relationship goes, Chilli said, “We broke up because I guess it was that time or whatever.” However, she still had deep feelings for him. She told Us Weekly, “I’ll always love him, forever, because he was my first adult love, a real love.”
Reality love
Chilli picked up the pieces and moved on. There were rumors she dated actor and author Hill Harper in 2006. Then, in 2008, she was linked to newly divorced CNN anchor T.J. Holmes. In 2009, she was spotted holding hands with former football player Larry Johnson. That relationship didn’t last long either. With a lack of suitable partners drying up, Chilli decided to take a different approach.
In 2010, she starred in her own reality show called What Chilli Wants. In an effort to find her dream man and future husband, she enlisted the help of dating coach Tionna Smalls. Chilli had impossibly high standards and didn’t want to date anyone who smoked, drank, or ate pork. On her dating checklist, she also included that her future partner had to have at least a 4-pack and be well-endowed.
She ended up choosing a guy named Bill, however that romance was short-lived. She told YBBG website they broke up after the show ended. She said, “There’s nothing wrong with Bill. There just wasn’t a connection.”
Dating rumors
Chilli was back on the scene and was spotted with Floyd Mayweather, but she insisted they were just friends.
In 2012, she starred in Tyrese’s music video for the song “Nothing On You.” Things got steamy on set, and a source told In Touch Weekly that they were an item. Tyrese shot that rumor down in an interview with The Boombox where he said Chilli was nothing more than a good friend.
In 2014, US Weekly broke the news that Chilli and comedian Wayne Brady were dating. According to a source, they were spotted holding hands at a TLC concert in Las Vegas. But Chilli’s rep and Wayne denied there was anything going on. It appeared that Chili was still on the market but not for long.
That following year, Chilli was rumored to be in a relationship with actor Brad James (pictured above). In 2016, Brad released a statement to Kontrol Magazine, saying there was another woman in his life that he had been seeing for a while. He also implied that Chilli was just another woman on his roster when he said, “Chilli, yeah, she’s amazing, and we are enjoying ourselves. So that is my status.”
Dating damaged goods
Chilli was on the move again. She appeared in Nick Cannon’s steamy music video for the song “If I Was Your Man.” Nick was still dealing with the aftermath of his divorce from Mariah Carey and apparently had no interest in ever getting married again. When People magazine asked him if he was dating Chilli, he was flattered but said he was damaged goods and just wanted to take things slow. He added, “More than anything, she’s somebody I care for and enjoy spending time with.”
Well, word on the street was that Chilli didn’t want to take things slow at all. She wanted to finally get married and settle down. A source told Life & Style website that Nick really liked Chilli and could even love her, but a ring was out of the question. That seemed like a deal-breaker because the relationship ended.
What’s next for Chilli?
As of this video, there are rumors that Chilli might be dating a man named Anthony Wilson, who just so happens to be Chris Brown’s manager. Whether this relationship works out or not, Chilli hasn’t given up on finding her Prince Charming.
In 2018, she confirmed to Essence magazine that she still holds on to her dating checklist, although it has grown even longer throughout the years. And since she considers herself a mixed woman with middle eastern and African-American ancestry, she’s not opposed to limiting herself to just black men. She gave some advice to other women who are looking for love, by saying, “God made all of us and you may not find your husband because you’re trying to stick to one group. You’ve got to be open.”
Chilli celebrated her 49th birthday in February 2020. Now that she’s older, wiser, and realizes all that she brings to the table, we have no doubt she’ll find her dream man and experience the beautiful wedding she has always desired.
Let us know your thoughts on Chilli’s dating history or drop us a comment on our YouTube channel.
Chilli will always have trouble finding a decent man who will want to settle down with her. She’s been f****d by everyone in the music industry and been on her knees more than most nuns! The stories about her promiscuity are legend and many and even she said that when she was kicked out of TLC, she was allowed back only on condition that she see a therapist for being “loose” and she wasn’t talking about her shoelaces!!
STFu you lying @$$ BOZO 🤡. What you just described is YOUR life story. Loose, ugly hoe…
Hey Chilli girl, how are you?
Well looks like she took her own advice in 2022. Finally.