Eight-time Grammy-winning singer Usher has tied the knot yet again. The R&B crooner is known for many things — from his chart-topping hits to his love life. Usher has always made his love and appreciation for the ladies clear, from crooning about them in songs to serenading them onstage. Over the years, the singer has been in various high-profile relationships, including with TLC’s Chilli to stylist Tameka Foster.
In February 2024, the “Caught Up” singer tied the knot to longtime girlfriend Jennifer Goicoechea after his monumental halftime performance at Super Bowl 58. This marriage marks Usher’s third trip down the aisle. Hopefully, the third time is the charm for the R&B singer. In honor of his 2024 nuptials, let’s take a look at Usher’s relationship history.
1. Chilli aka Rozonda Thomas (2001-2004)
Kicking off Usher’s relationship history is the Chilli saga. The former R&B power couple first met in 1993 while signed to the same recording label. However, their romance didn’t spark until 2001, with Chilli appearing in several of the singer’s music videos during his “8701” era. Usher admitted to being a huge fan of the iconic girl group member, even having a poster of her in his room as a kid.
The couple dated on and off for three years before eventually calling it quits in 2004. Shortly after the breakup, Usher released his hit album “Confessions,” with many speculating that cheating led to his split with Thomas. However, the TLC artist put those rumors to bed in a 2013 interview with Us Weekly.
“People assumed that album was about us, but it was not,” Chili told the outlet. “And Usher and I weren’t oil and water. We broke up because, I guess, it was that time or whatever. He was that real love for me.”
Although the couple split two decades ago, Usher says the breakup was extremely hard for him because Thomas turned down his marriage proposal, per TheJasmineBRAND. The former couple has reflected on their time together fondly, eventually moving on from that chapter of their lives.
2. Tameka Foster (2005-2009)
Usher began dating his fashion stylist Tameka Foster in 2005, later marrying her in 2007. Around the same time, the couple revealed they were expecting their first child together. Foster was already previously divorced and a mother of three. They tied the knot at an intimate ceremony in Georgia.
“He just accepted me for who I am,” said the stylist ahead of their wedding to Essence magazine. “I have flaws, I have an attitude problem.”
Usher sought to keep his relationship with Foster private, choosing not to divulge the details of their marriage and pregnancy at the time. Shortly after exchanging vows, their marriage was on the rocks, and Usher filed for divorce in 2009. The singer felt that their marriage was “irretrievably broken,” per divorce documents obtained by People magazine.
During their relationship, the couple welcomed two children: Usher V and Naviyd Eli.
3. Grace Miguel (2009-2018)
Shortly after his marriage to Foster ended, Usher began a relationship with his friend and longtime manager, Grace Harry, aka Grace Miguel. In 2015, Usher shocked fans with the news of his marriage to Miguel. The couple tied the knot in a private ceremony in Cuba.
In an October 2014 interview with Billboard, the singer revealed that his better half helped him through some trying times, professionally and personally. Three years after their secret wedding, the couple separated but remained close friends.
4. Jennifer Goicoechea (2019-Present)
Usher and his current leading lady, music executive Jennifer Goicoechea, first sparked romance rumors in 2019. A year later, the couple announced they were expecting their first child together, a baby girl named Sovereign Bo. He announced the wonderful news in 2020 via Instagram.
“We are feeling blessed and full of love with the arrival of our beautiful baby girl, Sovereign Bo Raymond. ‘Isn’t She Lovely’ by Stevie Wonder on repeat,” he wrote.
In 2021, the couple announced they were expecting their second child when Goicoechea accompanied Usher to the iHeartRadio Music Awards with a baby bump.
In October 2021, the couple welcomed the newest addition to the Raymond family, a son, Sire Castrello Raymond.
In February 2024, the singer married Goicoechea after he performed for halftime at Super Bowl 58. It was an intimate ceremony in Las Vegas, attended by only close family and friends. Per People magazine, the couple obtained a marriage license on Feb. 8, 2024, a few days before they tied the knot.
“Listen, when you find someone that you know is a great partner, of course, it is an honor and a pleasure to be able to share life with someone who wants to share it with you and loves you, who you are,” he said previously to People magazine.
Based on Usher’s relationship history, the singer is not afraid to follow his heart. He knows what he is looking for and is committed to finding it. We hope this new season of love and happiness continues to bloom for Usher.
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