Chilli & Usher: TLC Singer Stayed In Contact With R&B Star During His Marriage

BYHayley Hynes3.4K Views
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Chilli of TLC and Usher (Photo by James Devaney/WireImage)
Chilli told "PEOPLE" that she and Usher would often reconnect during periods when they were both single.

One of pop culture fanatics' favourite couples to watch over the past year has been Chilli and Matthew Lawrence. The unexpected duo first got together in 2022, shortly after he finalized his divorce from professional dancer Cheryl Burke. It's obvious that the TLC alum's feelings for Lawrence run deep, as she previously shared that she would be happy to marry him. While Chilli is more in love than ever before since beginning her new relationship, she recently revealed to PEOPLE that it took years to get over one of her past loves.

Usher seems to be the "one that got away" for the "No Scrubs" songstress, though they apparently remained in contact up until 2019 – even while he was married. "I love hard. I was like, ‘God, why can’t I get over this?’ He couldn’t either," she reflected to the outlet. Finally, Chilli got tired of repeating the same cycles and cut the Houston native off to "focus on [herself]." Not only did she quit Usher, but the 52-year-old "stopped dating" as a whole, proving how committed she was to her healing journey.

Chilli and Usher Have Plenty of History

Chilli and Usher during EMI Grammy Party Arrivals at The Blue Fin at The W Hotel in New York City. (Photo by Stephen Lovekin/FilmMagic)

"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," Chilli added. Prior to going no contact, she and the Confessions hitmaker could find themselves back in each other's lives during periods of being single.

While Chilli has been falling further in love with Matthew Lawrence, Usher has been living the dream during his Las Vegas residency. One of the most recent celebrity guests to get the up close and personal performance treatment from the vocalist is Baby Phat designer Kimora Lee Simmons. Read all about that at the link below, and check back later for more music/pop culture news updates.

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About The Author
Hayley Hynes is the former Weekend Managing Editor of HotNewHipHop, she stepped down after two years in 2024 to pursue other creative opportunities but remains on staff part-time to cover music, gossip, and pop culture news. Currently, she contributes similar content on Blavity and 21Ninety, as well as on her personal blog where she also offers tarot/astrology services. Hayley resides on the western side of Canada, previously spending a year in Vancouver to study Fashion Marketing at Blanche Macdonald Centre and Journalism at Mount Royal University in Calgary before that. She's passionate about helping others heal through storytelling, and shares much more about her life on Instagram @hayleyhynes.
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