Usher Is Married for the 3rd Time! Inside the Hitmaker’s Dating and Marriage History

Rozonda ‘Chilli’ Thomas

Usher and the TLC groupmate were one of Hollywood’s most loved couples from 2001 to 2004. This was the “Let It Burn” singer’s only high profile relationship.

Usher released his Diamond album the same year he and Chilli split, and fans were convinced that the tracklist was about their romance – especially “Confessions,” which is about being unfaithful in a relationship.

However, Chilli denied the decades-long cheating speculation in 2023 and shared what went wrong in their relationship.

“We definitely had some chemistry,” she told People at the time. “But working chemistry does not mean it works in your personal life. If we were working, it was great. But outside of that, we’re so different.”

The pair had bonded over their musical talent and success and Chilli was featured in Usher’s music videos for “U Got It Bad”, “U Remind Me” and “U Don’t Have to Call.”

Though they called it quits in 2004, Chilli and Usher ​were on-again and off-again, multiple times when they were both single until 2019.

In February 2024, Usher revealed that he proposed to Chilli, but it was anything but a fairytale.

“I wanted to marry her. I proposed and she told me no,” he told People at the time. “I went through a great deal of pain after that, not trusting women or wanting to open up.”

Tameka Foster

Usher became a family man after he ​wed wife No. 1, Tameka Foster, in 2007. Tameka worked as the “My Boo” musician’s stylist before starting a romantic relationship and the former couple welcomed kids Usher V and Naviyd Ely during their marriage.

Usher filed for divorce in June 2009 and it was settled later that year. The hitmaker remained silent about their separation until he gave a tell-all interview in 2012.

“Towards the end of our marriage, I found myself lost, and I just wanted out. No. I was faithful at heart, but not faithful all the way,” he said at the time. “Even having a conversation with another woman, period, about matters of your relationship or emotions is, in my opinion, not being faithful.”

Usher admitted that he was sexual with other women after they were separated but not officially divorced.

Grace Harry

Usher fell in love with another collaborator, Grace Harry ​(formerly known as Grace Miguel), who worked as his music manager. The two got married in September 2015 after they started dating shortly after his divorce from Tameka. Usher and Grace announced they called it quits in March 2018 and filed for divorce that December.

“After much thought and consideration, we have mutually decided to separate as a couple. We remain deeply connected, loving friends who will continue supporting each other through the next phases of our lives,” they said in a joint statement to Us Weekly in 2018. “The enormous amount of love and respect that we have for each other will only increase as we move forward.”

Jenn Goicoechea

Usher moved on to date Jenn in 2019, shortly after the crumble of his second marriage.

The pair welcomed their daughter, Sovereign Bo, in September 2020 and her younger brother, Sire Castrello, one year later.

“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,” the “Yeah!” singer told People in February 2024.