Rozonda “Chili” Thomas has been hailed as one of the classic beauties of our time and is also a part of one of the best selling girl groups, TLC.  She’s found success in different ventures, having hit singles along with her bandmates T-Boz and the late Left-Eye, as well as acting on shows such as The Parkers, Single Ladies, Living Single, and in films such as Snow Day and A Diva’s Christmas Carol.  Of all the areas of life she has been successful in, Thomas has seemed to be unlucky in love.

Over the years, the “Waterfalls” singer has been in some high profile relationships and hasn’t been shy of catching the brunt of relationship rumors.  Albeit maintaining a physique rivaled by many, even the younger generation, and being successful, it’s been lackluster in the love department.  

Chili began to famously date then super-producer Dallas Austin, with whom she also shares a son with.  Speaking with Vlad TV recently, Austin, who’s produced a great deal of TLC’s discography, shared tidbits on their relationship, which began during the recording process of their first album “Ooooooohhh… On the TLC Tip”.  

“I was doing the first album,” Austin began.  “We would hide it because, Pebbles wasn’t so crazy about the girls being groupies, and – you know, it’s hard for women in the industry to be dating producers and stuff.  So, we started dating, you know, we kept it away from her.  She didn’t know it, only the girls knew it.  And, it wasn’t until she got pregnant the first time and Pebbles found out, and then she kicked her out the group.”

Austin went on to say that he stood up for Chili to Pebbles after she began to hold auditions to find a replacement.  She would rejoin the group, but also after finding out she was pregnant, terminated her pregnancy, an action she would later admit was one of her “biggest mistakes” to VH1.  “It messed me up. It broke my spirit,” she recalled.

Chili, unable to forgive herself for what she had done, was determined to get pregnant again, and she and Austin became parents to their son Tron Austin in June 1997.  Their relationship wouldn’t last however and the couple called it off in 1999.

In what would perhaps be one of the most talked-about relationships in the media, Chili would end up dating Usher, beginning in 2001.  She even appeared in a few of his music videos such as “U Remind Me” and “U Got it Bad.”  Their relationship seemed to be perfect to many and fans began rooting heavily for their love.  

Things would take a turn when Usher began working on his biggest-selling album, Confessions, which was filled with themes of cheating within a relationship, including impregnating another woman.  While many assumed that Usher was letting it all hang out in terms of how his relationship with Chili became turbulent, she told US Weekly that the songs were in reality, about producer Jermaine Dupri and his love life.  “Usher was just singing it,” she said, “but people kind of bought into it.”

Fans were heartbroken to hear that the couple had broken things off as well.  While promoting the Confessions album on MTV, he addressed the rumors, saying “Yeah, I’m single. We’re still friends. It’s just something that happens in life.”  She also addressed the break-up with US Weekly saying, “We broke up because I guess it was that time or whatever.”  She, however, admitted to the magazine that she still cared deeply for him.   “I’ll always love him, forever, because he was my first adult love, a real love,”  she added.  However, there would be no reconciliation for the two, and she made it clear in an interview with The Bert Show in 2004 when she confessed, “Usher did the ultimate no-no to me. I will never be with him again, and that is that.” She didn’t stop there, adding, “He is so not-cute to me. I don’t ever want to see him again.”

There would be more rumors of dating celebrities after various sightings, like Hill Harper, CNN news anchor TJ Holmes, and football player Larry Johnson.  In 2010, she was the star of her own reality show, What Chili Wants, where she, alongside dating coach Tionna Smalls, would try to lock down a future husband.  On this show, viewers were able to witness the high standards she possessed when it came to dating, including not wanting to date anyone who smokes, drinks, and eats pork.  Her potential partner would also have to have at least 4-pack abs and had to be well endowed. 

The show produced a short-lived romance with a fella named Bill whom she chose.  “There’s nothing wrong with Bill,” she said in an interview. “There just wasn’t a connection.” 

One connection she has come forward however to say that she misses, and regrets losing, is with Marlon Wayans, whom many didn’t know she dated previously.  In a resurfaced interview with NecoleBitchie, she was asked if there was anyone that she let getaway, and hadn’t realized the guy was good until the relationship was over.  It was then that she made the revelation.  “This is gonna be big of me to say this. I have never ever said this in my whole life. Ever. But yea, I did let one good guy get away and that was Marlon Wayans.  See no one knew,” she exclaimed, “And it’s funny because I met Marlon when I was 20 when I had just got in TLC and you remember that movie “Mo Money”? I remember we were on tour with Hammer and we had went to the movies and I saw him in that movie. I was like ‘Oh My God he is soooo cute!!!’ So we went out that night and I ended up seeing him that night. And I met him for the first time and we just clicked instantly.

She went on to add that although Marlon was the one that got away, Usher was the one that she truly did love.  Wayans was then asked in a separate interview on his secret romance with the TLC star, and he responded that she was a “great person”, but didn’t go much further into detail about it.  “I’m gonna keep it funny and not philosophical on that type of stuff. You ain’t getting me in no fight. Look, n***a, you ain’t getting me in no fight!” joked Marlon.