Usher Reveals He Proposed To TLC’s Chilli Before Split
Usher revealed that Chilli from TLC “broke his heart” after she turned down his proposal after their split in 2004. The former couple dated from 2001 to 2004. Usher admitted…

Usher revealed that Chilli from TLC "broke his heart" after she turned down his proposal after their split in 2004. The former couple dated from 2001 to 2004. Usher admitted that he had a massive crush on the TLC singer and at age eight had a poster of her on his wall.
"If I am to be honest, I was her No. 1 fan, and she was my superstar," he told People, referencing lyrics from his 2004 hit "Superstar."
Due to both of their superstardom at the time, Usher said they were "missing each other" with their hectic schedules. He added that he wanted a "different type of relationship" where they could see one another, but it wasn't possible.
He continued to say that "she had very specific rules that didn’t work for me" and that "she didn't believe that I was actually in love with her as much as I was."
How Are Usher and Chilli's Relationships Now?
The pair was able to find love with other people. Currently, Chilli is dating actor Matthew Lawrence, who is known for his role in Boy Meets World. Usher just got married this past weekend in a surprise wedding to longtime girlfriend Jenn Goicoechea. The news follows the singer and music executive obtaining a marriage license on Feb. 8 in Clark County, Nevada.
The couple were first spotted together back in 2019 and later welcomed their daughter Sovereign Bo, in 2020, followed by their son, Sire Castrello, in 2021. Usher is also the father to sons Usher V and Naviyd Ely, with ex-wife Tameka Foster. Usher and Foster were married from 2007-2009. The R&B singer was also previously married to Grace Harry from 2015-2018.
"I have an amazing partner, a support system," Usher previously told the publication of Goicoechea. "We have an amazing dynamic between our relationship where I'm able to be passionate still about what I do and have an incredible partner to work through some of the harder times as a young man dealing with children."
While Usher is great to listen to, he's also not bad to look at either. Even after all these years, Usher is still giving us the same visuals we fell in love with when he dropped Confessions back in 2010. During his live performances, he is always putting on a show. We can't wait for one of the largest gigs of his career coming up in a couple of months.
Usher At The 2024 Super Bowl
While Usher has been doing his thing during his Las Vegas residency and performing several festivals over the summer, he is now going to take his talents to the world's largest stage: The Super Bowl. Last month it was announced that Usher will be staying in his second home of Las Vegas a little bit longer as he will be the Super Bowl LVIII headliner.
"It's an honor of a lifetime to finally check a Super Bowl performance off my bucket list," Usher said in a press release. "I can't wait to bring the world a show unlike anything else they've seen from me before. Thank you to the fans and everyone who made this opportunity happen. I'll see you real soon."
Jay-Z, who signed a multi-year partnership with the NFL through his label Roc Nation, praised Usher's longstanding legacy in the music industry.
"Usher is the ultimate artist and showman. Ever since his debut at the age of 15, he's been charting his own unique course. Beyond his flawless singing and exceptional choreography, Usher bares his soul," said JAY-Z. “His remarkable journey has propelled him to one of the grandest stages in the world. I can't wait to see the magic.
Usher's new album Coming Home, will also be released on the day of the Super Bowl: February 11, 2024. Songs such as "Good Good," "Boyfriend," and "GLU" will be featured on the album.
He is also reportedly going on tour after the Super Bowl in support of his new album so you just might be able to witness these sexy Instagram looks in person.
Take a look at seven of his sexiest Instagram photos below:
7.
Paris Fashion Week never looked this good. The Confessions creator attended the luxury designer event earlier this year and he did not come to play. Usher wore several outfits over the course of the week including a black and blue blazer, a tan leather suit, and even switched up his hair color to an orange during his time overseas.
6.
It's the confidence for us. One of Usher's greatest traits is that he knows how to put a fit on. He wore leather joggers with a loose oversized white tank and a matching jacket. But, it was truly the accessories that made the outfit even sexier. The white shoes, diamond chains, and oversized sunglasses brought the outfit to the next level.
5.
We love a shirtless moment. This photo is from his annual Lovers and Friends Festival which is hosted in Vegas every year. If Usher has more moments like this on stage next year, we are ready to pack our bags and head over to Sin City.
4.
There's something about Usher on this motorcycle that does something for us! The Grammy-winner was the cover star for Zeit Magazin, which is a Germany-based publication. In this Instagram post, Usher also showed more shots from the photoshoot, such as a shirtless photo with him in dress pants, him in an all-black outfit standing next to a car, and a playful shot of him sticking his tongue out. (Don't mind us just hopping on a flight to Germany to pick up a copy).
3.
Usher recreated his "Nice & Slow" single cover in honor of its 25th anniversary and we can't tell the 1997 version from this 2022 photo. In both photos he is wearing his iconic "U" chain as he poses shirtless (thank you for that, Usher). And to answer his question in the caption, at 7 pm on the dot, Usher was in his "drop top, cruising the streets."
2.
If one thing Usher still has its his "IT" factor. He performed one of his latest songs "GLU" at the Dreamville festival back in April when he so conveniently took off his shirt before performing. Let's just say we have suddenly forgotten all the words.
1.
What is the sexiest photo on his Instagram? Easy: this shirtless photo of him standing in a warehouse. His glaring focus into the camera, the sun outlining his body, and now we are all so suddenly jealous of the towel hung on his neck. No caption needed *mic drop*.