When singers Usher and Chilli were dating, everyone thought they were the perfect couple. They dated from 2001 to 2004, and many assumed the pair in the match made in heaven would eventually tie the knot due to their deep passion and love for each other.
Even Chilli herself admitted they had an undeniable “chemistry” in an interview last year. The TLC singer said it ultimately didn’t work out because they were “different.” Although cheating and infidelity on Usher’s part marred their relationship, neither has addressed the exact reason for their split. But the “Yeah!” singer’s latest interview adds some context to what took place.
In a recent interview with People magazine, Usher revealed that he’s always had a thing for older women and that he once proposed to Chilli.
“I wanted to marry her. I proposed, and she told me no,” he admits. “I went through a great deal of pain after that, not trusting women or wanting to open up.” He confessed, “I hurt her too,” but the situation “broke my heart.”
Chilli stated that they remained on and off for years after the split. But for Usher, his trust was broken after the time of the breakup.
“We were cool with each other, but I was very careful with that. I really did love that girl,” he shared, “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.'”
There was a seven-year age gap between the two entertainers, though Usher, now-45, seemed to have a knit for charming women with his seductive R&B lyrics.
“I was always charming the older ladies,” he admitted. “If I am to be honest, I was her No. 1 fan, and she was my superstar,” he continued, which could have been the inspiration for the fan-favorite “Confessions” track “Superstar.”
Usher really has a thing for older women.
— 💋RayBay💋 (@MsRayBay) February 15, 2024
“I was a young man, and she had very specific rules that didn’t work for me,” he says. “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.”
Usher’s self-titled 1994 debut album included titles such as “I’ll Make It Right,” “I’ll Show You Love,” “Slow Love,” and more. He moved from his hometown in Chattanooga, Tennessee, to Atlanta, upon being discovered by legendary producer L.A. Reid, who signed him to his old label LaFace Records, which was later acquired by Arista.
He went on to release eight more studio albums such as “My Way,” when he was 18, followed by “Confessions,” “Raymond v. Raymond,” “Looking 4 Myself,” “Hard II Love,” and more. He has worked closely over the years with the likes of Grammy-winning singers, songwriters, and producers, including Jermaine Dupri, Bryan-Michael Cox, Jimmy Jam, and Terry Lewis. His most recent album, “Coming Home,” was released earlier this month.
The 2004 “Confessions” album, fueled by cheating accusations, arrived during his highly publicized relationship with Chilli.
“I’m not hurt over that at all,” Usher added before revealing that he and Chilli have “since become cool with each other, celebrate each other and it’s always light when we see each other.”
Chilli is currently dating former “Boy Meets World” actor Matthew Lawrence, and her TLC bandmate could not be happier for her. “I’m living vicariously through her, so it’s been great ’cause I’ve never seen her like this, and I’ve been there 31 years. I’ve seen it all, honey. We’ve been through life together,” said Tionne “T-Boz” Watkins at the 2023 iHeartRadio Music Awards.
She has one son, Tron Austin, with her ex, music producer Dallas Austin.
Usher has four kids: two teenage boys from his second marriage to image consultant Tameka Foster, who is eight years his senior, and two younger children with his longtime partner, music executive Jennifer Goicoechea, who is five years younger than Usher. The two began dating in 2019 and got married over the weekend after his halftime performance at the Super Bowl LVIII.
Usher 's Ex – wife Tameka foster thought he was already married to Jennifer Goicoechea pic.twitter.com/uHo5i81J1P
— Dominic Benjamin obinna (@DominicBen40381) February 15, 2024
He was also previously married to his former manager, Grace Miguel, from 2015-2018.
