Usher Reveals He Was Heartbroken After Chilli Declined To Marry Him

By Tony M. Centeno

February 15, 2024

Usher & Chili
Photo: Getty Images

Usher had it bad when his former dream girl Chilli declined his marriage proposal.

In an exclusive excerpt from People's cover story that was published on Thursday, February 15, the Coming Home singer opened up about his former relationship with the TLC singer, born Rozonda Thomas. The couple dated from 2001 to 2004, which is the same year his iconic album Confessions impacted pop culture. Usher said Chilli, who was seven years older than him when they dated, "didn't believe that I was actually in love with her as much as I was." He even admitted that he proposed to her.

“I wanted to marry her," Usher shared. "I proposed and she told me no. I went through a great deal of pain after that, not trusting women or wanting to open up.”

"We were cool with each other, but I was very careful with that," he continued. "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.'"

Usher Raymond, who's now 45, recalled that he "hurt her too," however, the end of their relationship truly "broke my heart." It looks like Chilli's loss was his new wife's gain. Following his historic performance at the Super Bowl LVIII Halftime Show, the Grammy award-winning singer married his longtime girlfriend Jennifer Goicoechea during a private ceremony in Las Vegas. The couple celebrated the occasion with Usher's mother, their kids and other close friends during a closed celebration and at Dr. Dre and Snoop Dogg's Super Bowl after party.

Check out Usher and Jennifer's wedding photos below.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.