Usher reflects on past relationships in recent ‘Confessions’

In a series of recent interviews, Usher opened up about his past relationships, a failed proposal and more.

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Usher performs onstage during the Apple Music Super Bowl LVIII Halftime Show at Allegiant Stadium on Feb. 11, 2024, in Las Vegas, Nevada. (Photo by Harry How/Getty Images)

Following his Super Bowl Halftime show performance, the streets have been buzzing about “Ursher baby” — only now, Usher’s love life and previous partners have risen to the forefront of the conversations. While the star is celebrating a successful performance, upcoming tour, and recent nuptials to his longtime girlfriend Jennifer Goicoechea, he has also been sharing some new confessions about his past. 

In an interview with People magazine, Usher discussed his past relationship with TLC’s  Rozonda “Chilli” Thomas. Having dated from 2001 to 2004, the “My Way” singer explained why their relationship ended despite his deep love for his celebrity crush-turned-girlfriend. 

“If I am to be honest, I was her No. 1 fan, and she was my superstar […] I was a young man, and she had very specific rules that didn’t work for me,” he told the publication, explaining how distance played a part in their downfall. “She didn’t believe that I was actually in love with her as much as I was. I wanted to marry her. 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.”

While reflecting on his heartbreak, Usher shared his wrongdoings in the relationship. Realizing his actions weren’t meeting Chilli’s romantic expectations, he admitted that he “hurt her too” in the relationship. 

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Usher would subsequently move on to date other women, including his ex-wife Tameka Foster. The R&B singer and Foster, his stylist at the time, began dating a few years after his romance with Thomas. Getting married in 2007 and divorced in 2009, the couple share two children, Usher V, 16, and Naviyd, 15. Despite a previous custody battle, Usher explained that he and his ex-wife are now cordial. 

“We ain’t good, good, but we good. You know what I’m saying?” he said, quoting his song “Good, Good,” featuring Summer Walker and 21 Savage. 

Foster echoed these sentiments on Sunday as she supported her ex-husband’s Super Bowl Halftime show performance. 

“I think that he did amazingly well … I did not notice one — I mean, not one — blemish in the performance,” she said, per People magazine. “I don’t think people realize that he’s singing live and doing all of this stuff. So that’s one thing that really needs to be taken into consideration. The mic is always on when he’s around, he can sing for real. It was beyond… above anyone’s expectations.”

While Foster sang Usher’s praises, the stylist, who previously worked with the likes of Jay-Z, Mary J. Blige and Patti LaBelle, couldn’t help but comment on his fashion choices for the performance. As the R&B star performed a medley of his greatest hits, Usher sported custom looks from Off-White, Louis Vuitton, and Dolce & Gabbana. 

“His looks were great… I thought he looked nice,” the fashion stylist says. “The only comment I had is that I wish that his opening outfit was a little more slim fit — not small, but a little slimmer, just because I really prefer to see lines on dancers when people are dancing. I like to see the lines of their physique. But aside from that, I loved the outfits. I loved the opening, the overcoat, everything.” 

Having been in the industry for nearly 30 years, the Super Bowl headliner has learned how to protect his personal life from the spotlight, especially after facing backlash from fans for his relationship with Foster. 

“I think I became very closed and then felt attacked in many ways,” Usher explained. “It was a bit unconventional in a time when I felt like my female fans were judgmental of the woman that I chose.”

However, Usher always chose to share his experiences in his music. According to the star, “there is a great deal of truth” in one of his most notable albums, “Confessions.” Released in 2004, the album reportedly haphazardly recounts one of Usher’s past relationships while including topics inspired by “real talk sessions” the star had with producer Jermaine Dupri and other male friends in the industry. 

“[Publicist Chris Chambers] motivated me to think about who I was and what people knew about me. And the result of that was ‘Confessions’,” he revealed to People magazine. “Prior to that conversation, I had always felt like I would be judged as a result of being vulnerable. Black men, we deal with this. […] We go through things in life, and sometimes we make decisions based off of what we feel is best or right and more than likely, will best serve the child. But the reason why I talked about it is because I’m not the only person who will experience that as men.” 

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