Six months ago, Usher Raymond said one of the hardest things for him to do is be “single.” At the same time, the R&B singer recently revealed that his struggles with trust began after one of his most beloved partners rejected his marriage proposal.
Usher has been in several highly publicized relationships, many of which involved infidelity on his part. However, he recently revealed that his commitment issues and distrust in women began early on in his 20s.
Still, the hopeless romantic and now father of four never gave up on love, and while he has been married twice before, he hopes that the third time is the charm.
Here’s a look back at Usher’s past marriages and relationships and where his distrust in women began.
Jennifer Goicoechea, 2019 to Present
On Sunday, Feb. 11, hours after he would make history with his halftime performance at Super Bowl LVIII, the second-most viewed television broadcast in U.S. history, Usher married his longtime girlfriend, Jennifer Goicoechea.
The two have been dating since 2019 and share two children, Sovereign Bo, 3, and Sire Castrello, 2.
“We’ve obviously made a commitment to life for life together because of our children,” Usher told People magazine. “It wouldn’t be odd for us to get married. We already did here. You know what I’m saying?”
Rumors that Usher tied the knot started floating days ahead of his Las Vegas performance. They reportedly obtained their marriage license on Feb. 8 but didn’t make an official announcement on Instagram until Valentine’s Day, posting pictures from the nuptial for his 12.9 million Instagram followers to see.
“I’m very happy, very fortunate to have an incredible friend, not just a partner,” he continued. “She’s my best friend, and I love her.”
He added, “We have any 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 and dealing with the dynamic of how you communicate with them.”
The Grammy-winning vocalist and Jennifer can be seen kissing in the first picture, followed by pictures of their children, including Usher’s oldest two sons, Usher “Cinco” V, 16, and Naviyd Ely, 15, whom he shared with his second wife, Tameka Foster.
Grace Harry, 2009 to 2018
Usher began a relationship with Grace Miguel, now known as Grace Harry in 2009. Much is not known about this relationship except at one point Harry served as his manager. The two eloped in 2015 just months after Usher proposed and were in divorce court three years later.
The “Hard II Love” singer and his ex-wife, who have kept quiet about their past together, signed a confidentiality agreement as part of the divorce, which stops them from speaking ill about each other in the media. They also made sure that people knew that there was no bad blood between them.
“After much thought and consideration, we have mutually decided to separate as a couple,” they said in a joint statement at the time of their separation. “We remain deeply connected, loving friends who will continue supporting each other through the next phases of our lives. The enormous amount of love and respect.”
Tameka Foster, 2005 to 2009
Usher’s teenage boys were also in attendance with his first wife, their mother, Tameka Foster, for his Super Bowl performance.
“One of the perks of having Usher as an ex is going to the Super Bowl,” she said in an interview with Page Six.
Like Harry, his first wife was someone that he had met in the industry. Usher married the woman who was once his stylist before becoming his friend in 2007. Their friendship blossomed into something romantic, and from it the two welcomed their two boys. While her ex gifted her with VIP tickets to the game, it was not always harmonious.
The former couple had a vicious post-divorce season where they seemed to have fought mostly over custody issues and co-parenting. During those first few years after their split, Usher had primary custody, and the image consultant complained that she did not have enough input in the kid’s rearing.
The custody battle endured even during Foster’s grief about her son Kile Glover, who was killed after being hit by a jet ski.
Though the union lasted for only two years and seemed to end ugly, both admit that at one time they were madly in love.
The “My Way” singer often doted on his wife, telling his fans on major platforms like MTV’s “Total Request Live” that he loved her “very much,” while dismissing ill rumors about her.
“I’m tired of people continuing to talk so much trash about me, know what I’m saying? And my relationship,” he said. “My wife is not 40 years old. I love her to death and I’m a Black, strong man in America standing up for my people — as a man to my wife, to my son, to my family.”
He continued, “I’m making a stand that a lot of us should make. I coulda been like any other man who has a child and live with that woman and continue to just play the game. … I’m trying to do it the right way. This is the way your supposed to do it!”
While Usher and Foster were dating he also ended his business relationship with his mother, Jonetta Patton, who had served as his manager. In response to critics who believed Foster created a wedge in his relationship with his mother, he said at the time, “And my wife had nothing to do with me firing my mother — nothing like that, that’s trash.”
He said he was also “hurt” his mother chose not to attend their wedding ceremony in 2007. He ended up canceling the planned ceremony and getting married in a private ceremony. There were also other “trash” rumors about Foster, including gold digger accusations and allegations she married Usher for his money, a claim that she totally disputes.
Usher admitted to Oprah Winfrey in 2012 that he did cheat on Foster toward the end of their marriage.
“Towards the end of our marriage, I found myself lost, and I just wanted out,” he said.
“I was faithful at heart,” the chart-topper said. “But not faithful all the way. Even having a conversation with another woman, period, about matters of your relationship or emotions is, in my opinion, not being faithful.”
Usher further admitted he cheated during a time when they were “separated” and not yet divorced. Although they were once “enemies” and have been divorced since 2009, he claims he and Foster are now “cordial with each other. We ain’t good, good, but we good. You know what I’m saying?”
Chilli, 2001 to 2004
One notable relationship in Usher’s history was with his former label mate Chilli from TLC. They crossed paths after Usher joined LaFace Records under L.A. Reid’s management and were romantically involved for three years.
In multiple interviews, Chilli has mentioned that a contributing factor to their relationship’s dissolution was that they only had “working chemistry.”
“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 different,” the “Ain’t to Proud to Beg” singer said.
The singer, who is currently dating actor Matthew Lawrence, said that she and Usher had different value systems, which added to why their relationship didn’t work.
“It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” Chilli added.
Usher said he tried to get it right for her.
“I really did love that girl and I was like, ‘I don’t want to play with you,’” he said, adding, “I did everything that I thought you would’ve wanted me to do, but I guess my good wasn’t great enough.’”
During Usher’s #SuperBowl #HalftimeShow if he brings out Chilli of TLC to “U Remind Me” & or “U Got It Bad” since she was in the videos, I would flip!
— Jerome Trammel (@MrJeromeTrammel) February 11, 2024
They’re in relationships so I know it won’t happen. But, it’ll be an iconic & nostalgic moment. We still want them to work.. 😅 pic.twitter.com/hRW5psARrH
Usher admitted that he was in love with Chilli in a recent interview and was devastated about the demise of their relationship, which made him develop a distrust of women.
“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.”
According to Chilli, another narrative said over the years about their breakup was not true. Many said he was unfaithful. The chart-topper, whose group is the fifth best-selling girls group in the world, said Usher never cheated on her.
But according to him, he did hurt her. Even though the “Confessions” artist said he hurt her, he was the one damaged by the breakup, mostly because he could never figure out how to give her what she wanted.
Regardless, it looks like Usher has rebuilt his trust in women to form a family with his new wife Jennifer.
