Usher reveals proposal to TLC's Chilli, eventual rejection

Some Usher confessions: R&B icon reveals proposal to TLC’s Chilli, eventual rejection

Usher smiling and wearing big square sunglasses, a black leather jacket and gloves. He is holding a microphone

Feb. 15, 2024 2:46 PM PT

Usher, just days after marrying music executive Jennifer Goicoechea, says ex-girlfriend and TLC singer Rozonda “Chilli” Thomas was the one who got away.

The “Confessions” and “Yeah!” singer, 45, revealed that he proposed to fellow musician Thomas, 52, during their relationship in the early 2000s. “I really did love that girl,” Usher said while revisiting his romantic history for People.

The Grammy winner, who said he fantasized about meeting the singer when he was a kid, began dating Thomas — one-third of TLC — in 2001. They dated for three years, eventually breaking things off in 2004. The highs and lows of their romance went on to inform Usher’s 2004 hit release, “Confessions.” At the time of their split, Usher (real name Usher Raymond IV) said he and Thomas were at different stages of their lives.

“I was a young man, and she had very specific rules that didn’t work for me,” he told the magazine. “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.”

Despite their differences, Usher revealed that at one point he wanted to spend the rest of his life with Thomas. “I wanted to marry her,” he said, “I proposed and she told me no.” In case it wasn’t already clear from songs like “Burn” and “My Boo,” Thomas’ rejection left Usher in his feelings.

He added: “I went through a great deal of pain after that, not trusting women or wanting to open up.”

More than 20 years since their split, both Usher and Thomas have moved on. In 1997, Thomas and producer ex-boyfriend Dallas Austin welcomed son Tron Austin, who is expecting a child of his own. Most recently, Thomas began dating “Mrs. Doubtfire” actor Matthew Lawrence.

Usher went on to marry fashion designer Tameka Foster in 2007. They welcomed sons Usher Raymond V and Naviyd Ely, but divorced in 2009. After Foster, Usher wed writer Grace Harry. They were married from 2015 to 2018.

The “Coming Home” singer tied the knot for a third time — this time to Goicoechea, 40 — just hours after his Super Bowl LVIII halftime spectacular on Sunday. A representative for the singer confirmed to The Times on Tuesday that the newlyweds were “surrounded by close friends and family” for their Las Vegas nuptials.

“They both look forward to continuing to raise their children together surrounded by love and thank everyone for the well wishes,” the representative added.

Usher celebrated his wedding on Instagram, sharing photos from the secret ceremony. Usher’s photos show the singer and Goicoechea sealing the deed with a kiss and posing with their loved ones.

“One of them Ones 💍 2.11.24,” Usher captioned his post.