Close Menu
The Shade RoomThe Shade Room
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • NEWSLETTER
  • CAREERS
  • ADVERTISE WITH US
  • GET FEATURED
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Trending
  • Celeste Rivas Hernandez’s Father Addresses Claims Of Contact With D4vd & Receiving Alleged Payments (VIDEO)
  • Spirit Airlines Shuts Down & Cancels All Flights Amid Reports Of Financial Setbacks (VIDEOS)
  • Suspect Reportedly Arrested After Shots Fired Outside Of Chris Brown’s Los Angeles Home (PHOTOS)
  • End Of An Era! Fans Sound OFF As ‘Love & Hip Hop’ Franchise Is Reportedly Set To End After 15-Year Run (PHOTO)
  • Oop! Social Media Thinks 21 Savage Responded To GloRilla’s Sister After She Made Claims About Latto’s Pregnancy (PHOTO)
  • Too Cute! OMB Peezy Goes Viral Following Emotional Reaction To His Girlfriend Acing Her Final Exams (VIDEO)
  • Wayment! Domino’s Delivery Driver Faces Charges After Allegedly Hitting Customer With His Car Over Tip Dispute
  • Girl, BYE! Jayda Cheaves Sets The Record Straight After TikTok User Criticizes Her Appearance (VIDEOS)
  • Still Going Strong! Fans Call Halle Bailey’s Boyfriend Scott Bridgeway An “Upgrade” After ASCAP Awards Date Night (PHOTOS)
  • Celeste Rivas Hernandez’s Family Shares Statement As Gruesome Details About Her Final Moments Emerge (VIDEO)
The Shade RoomThe Shade Room
The Shade Room Text Logo
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • ADVERTISE WITH US
The Shade RoomThe Shade Room
Home » Latest Tea » Chilli Reportedly “Unbothered” By Usher’s Proposal Reveal, Enjoys Vacation With Matthew Lawrence
Celebs

Chilli Reportedly “Unbothered” By Usher’s Proposal Reveal, Enjoys Vacation With Matthew Lawrence

Cassandra SantiagoBy Cassandra Santiago2024/02/16
Facebook Twitter Pinterest LinkedIn Tumblr Email
Chilli Curves Usher's Proposal Reveal, Enjoys Trip With Matthew
L: LOS ANGELES, CALIFORNIA - MARCH 09: Matthew Lawrence (L) and Chilli Thomas attend as Lifetime Celebrates Black Excellence with their Female Creatives and Talent at the +Play Partner House on March 09, 2023 in Los Angeles, California. (Photo by Randy Shropshire/Getty Images for Lifetime) R: ATLANTA, GEORGIA - FEBRUARY 14: (EDITOR’S NOTE: Image created using a star filter) Usher attends The Black Music And Entertainment Walk Of Fame Honors Usher at Black Music and Entertainment Walk of Fame on February 14, 2024 in Atlanta, Georgia. (Photo by Prince Williams/FilmMagic)
Share
Facebook Twitter LinkedIn Pinterest Email

And there ya have it! Sources who spoke to PEOPLE and TMZ seemingly confirmed that Chilli peeped Usher’s stroll down memory lane. However, the TLC star is allegedly “unbothered” about the world knowing she turned down his marriage proposal.

A source close to Chilli reportedly told PEOPLE: “Chilli is unbothered by the recent hoopla involving her past relationship.”

Meanwhile, “sources with direct knowledge” shared similar sentiments with TMZ, saying she hasn’t given the marriage proposal story a second thought.

In fact, the TLC singer has been living it up in Jamaica with her new man, ‘Boy Meets World’ actor Matthew Lawrence. The pair enjoyed a dual birthday and Valentine’s Day getaway at the Sandals Dunn’s River resort this week. Lawrence celebrated his 44th birthday on Feb. 11.

Keep scrolling to see a few baecation photos.

Chilli Enjoys Trip With Matthew AMid usher Proposal Reveal
OCHO RIOS, JAMAICA – FEBRUARY 10: (Photo by John Parra/Getty Images for Sandals Resorts)

 

Chilli Enjoys Trip With Matthew AMid usher Proposal
(Photo by John Parra/Getty Images for Sandals Resorts)

 

Chilli Enjoys Trip With Matthew AMid usher Proposal Reveal
 (Photo by John Parra/Getty Images for Sandals Resorts)

Usher Says Chilli Caused Him “A Great Deal Of Pain” After Failed Proposal

For context, Usher revealed he was heartbroken after Chilli shut down his attempts to marry her in the early 2000s. The former pair, who are seven years apart in age, reportedly began dating in 2001. Their relationship ended in 2004, sometime after Chilli rejected his proposal. Her rejection caused him “a great deal of pain,” Usher told PEOPLE.

“I was a young man, and she had very specific rules that didn’t work for me,” Usher told PEOPLE. “We were missing each other. I really did want to have a different type of relationship where she was there with me, and she couldn’t be. She didn’t believe that I was actually in love with her as much as I was.” 

Chilli told the same outlet last year that she and Usher dealt with each other on and off after the split. However, in his recent interview, the ‘Confessions’ singer said though they remained “cool,” he kept his emotions guarded after the failed proposal.

“We were cool with each other, but I was very careful with that. I really did love that girl, and I was like, I don’t want to play with you. Like, ‘I can’t give you what I gave you. I did everything that I thought you would’ve wanted me to do, but I guess my good wasn’t great enough.” 

Despite dropping this truth bomb via PEOPLE, Usher himself has moved on from the 20-year-old split. After putting on the most-watched Super Bowl performance ever, he secretly married his girlfriend Jennifer Goicoechea in a Las Vegas drive-thru ceremony.

RELATED: Usher Clarifies Relationship With Chris Brown After Addressing Rumors Of A Super Bowl Show Invite (Video)
What Do You Think Roomies?
+1
0
+1
0
+1
0
+1
0
+1
0
+1
0
+1
0

Share. Facebook Twitter Pinterest LinkedIn Tumblr Email

Related Posts

Celeste Rivas Hernandez’s Father Addresses Claims Of Contact With D4vd & Receiving Alleged Payments (VIDEO)

2026/05/02

Spirit Airlines Shuts Down & Cancels All Flights Amid Reports Of Financial Setbacks (VIDEOS)

2026/05/02

Suspect Reportedly Arrested After Shots Fired Outside Of Chris Brown’s Los Angeles Home (PHOTOS)

2026/05/02
Latest Posts

Celeste Rivas Hernandez’s Father Addresses Claims Of Contact With D4vd & Receiving Alleged Payments (VIDEO)

2026/05/02

Spirit Airlines Shuts Down & Cancels All Flights Amid Reports Of Financial Setbacks (VIDEOS)

2026/05/02

Suspect Reportedly Arrested After Shots Fired Outside Of Chris Brown’s Los Angeles Home (PHOTOS)

2026/05/02

End Of An Era! Fans Sound OFF As ‘Love & Hip Hop’ Franchise Is Reportedly Set To End After 15-Year Run (PHOTO)

2026/05/02

#TSRExclusive

Not you missing out on our newsletter, tap in & sign up!

About
About

TSR is the culture's definitive source for trending celeb news, exclusive interviews, videos, and more.

NMSDC CERTIFIED

Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Latest Posts

Celeste Rivas Hernandez’s Father Addresses Claims Of Contact With D4vd & Receiving Alleged Payments (VIDEO)

Spirit Airlines Shuts Down & Cancels All Flights Amid Reports Of Financial Setbacks (VIDEOS)

Suspect Reportedly Arrested After Shots Fired Outside Of Chris Brown’s Los Angeles Home (PHOTOS)

Featured Posts

Too Cute! OMB Peezy Goes Viral Following Emotional Reaction To His Girlfriend Acing Her Final Exams (VIDEO)

Wayment! Domino’s Delivery Driver Faces Charges After Allegedly Hitting Customer With His Car Over Tip Dispute

Girl, BYE! Jayda Cheaves Sets The Record Straight After TikTok User Criticizes Her Appearance (VIDEOS)

© 2026 The Shade Room
  • Celebs
  • News & Politics
  • Beauty & Style
  • Shows
  • TSR Teens
  • TSR Shop
  • Privacy Policy
  • Terms & Conditions
  • Advertising Guidelines

Type above and press Enter to search. Press Esc to cancel.