From Failed Marriages To A Declined Proposal And A Super Bowl Wedding: A Look At Usher’s Relationship Timeline

BY Abena Dzaka February 20, 2024 2:20 PM EDT
Photo Credit: Facebook @Usher

Usher Raymond claimed that being “single” was one of the hardest things for him to do just six months ago.

Simultaneously, the R&B musician also disclosed that his trust issues started when one of his closest companions turned down his proposal of marriage.

Usher has been in several relationships, many of which ended due to reports of him being unfaithful. But he recently disclosed that his mistrust of women and commitment problems started in his early twenties.

Despite having been married twice before, Usher never gave up on love and hopes that his third marriage will be the last. Here is a look back at Usher’s relationship timeline.

Jennifer Goicoechea: 2019 – Present

Usher married Jennifer Goicoechea, his longtime girlfriend, on Sunday, February 11, just hours before he would create history with his halftime show at Super Bowl LVIII, the second-most watched television show in American history.

Sovereign Bo, age three, and Sire Castrello, age two, are the couple’s two children. They started dating in 2019.

Usher told People magazine, “We’ve committed to living life together because of our children. It wouldn’t be strange if we tied the knot. Here, we have already done so.”

Days before his performance in Las Vegas, there were rumors that Usher had tied the knot. According to reports, the duo got married on February 8 but didn’t officially announce it on Instagram until Valentine’s Day. He shared photos from the wedding with his 12.9 million Instagram followers. 

Grace Harry: 2009 – 2015

In 2009, Usher started dating Grace Miguel, who is currently known as Grace Harry. Apart from the fact that Harry was his manager at one point, not much is known about this relationship. Three years after Usher’s proposal, the couple entered divorce court. They had eloped in 2015.

As part of the divorce settlement, the singer of Hard II Love and his ex-wife, who has not spoken publicly about their relationship, agreed to sign a confidentiality agreement prohibiting them from disparaging each other in public. Additionally, they took care to ensure that everyone was aware of their amicable relationship.

Tameka Foster: 2005 – 2009

Similar to Harry, Usher had met his first wife in business. In 2007, Usher married the woman who had been his stylist before they became friends. After their friendship developed into a passionate relationship, the couple welcomed two boys.

The former couple appeared to have fought primarily over co-parenting and custody issues during their acrimonious post-divorce season. Usher had primary custody of the children during the initial years following their divorce, and the image consultant expressed dissatisfaction over her lack of involvement in their upbringing. 

Even though their marriage appeared to end badly and lasted only two years, the former couple acknowledged that they were once deeply in love.

Chilli: 2001 – 2004

Usher had a noteworthy relationship with Chilli from TLC when they were labelmates. Following Usher’s signing to LaFace Records, which was managed by L.A. Reid, they became acquainted and dated for three years.

In numerous interviews, Chilli has stated that their lack of “working chemistry” was one of the reasons behind the breakup.

In a recent interview, Usher acknowledged that he was in love with Chilli and expressed his sadness over their breakup, which led to him growing mistrustful of women. 

“I desired to wed her. I asked her out, and she said no. After that, I experienced a lot of pain; I didn’t want to open up to women or trust them,” said Usher.

Chilli asserts that an alternative account of their breakup that has been floating around for a while is untrue. Many claimed he was disloyal. Usher never cheated on her, according to the chart-topper, whose group is currently the fifth best-selling girls group worldwide.

The singer claimed that one of the reasons their relationship didn’t work out was that she and Usher had different value systems. The singer is currently seeing actor Matthew Lawrence.