Usher Raymond was definitely one of the most sought-after R&B singers. It would take nothing for Usher to titillate his female fans. From his skillful vocal abilities to his chiseled body and smooth dance moves, Usher was the dream man for many women. While there may have been many relationships that the public is not aware of, Usher has had quite a few high profile relationships. Many of us have grown with and/or watched Raymond grow, and throughout his almost 30-year career, have seen how the relationships have played out. Four kids later, let’s take a look back at the Diamond-certified singer’s relationships.
In the past, the “Let It Burn” singer has been romantically linked to other celebrities such as Brandy, Jade Ewen, and Naomi Campbell. Usher had also been rumored to have been dating Baywatch star Pamela Anderson in 2006. However, this was proven to be false, but Anderson was reportedly both shocked and pleased with the rumor! Multiple news outlets report her reacting to the news saying, “Oh gosh, that’s a good story. Keep that one going! I haven’t heard that one before. Usher! Well, he is hot.”
Diehard fan or not, many remember Usher’s relationship with TLC member Chilli. Back in 2001, Usher and Chilli’s romance was the talk of the town and perhaps relationship goals for many. The beautiful couple were seen everywhere from award shows to various other events. However, their romance would fizzle while rumors of infidelity began to spark in the media. The release of his Confessions album, the biggest album in his career, would only heighten and lead to their break-up.
A 2004 interivew on Atlanta radio station Q100’s The Bert Show brought Chilli to reveal that Usher had committed the “ultimate no-no”, causing them to split. “I will never be with him again, and that is that,” the award-winning entertainer said. “He portrayed himself to be this honest and great guy, and he really wasn’t.”Despite their very public break-up, Usher was able to find love once again. This time, his beau was not a high-profile artist. However, being romantically linked to one of the biggest stars on the planet will get you there. Tameka Foster, Usher’s personal stylist at the time, captured Usher’s heart around November of 2005. Coming from his relationship with Chili, the fans were not so pleased. Reportedly joining the displeasure of the relationship was Usher’s mother, who was said to have not attended their wedding.
This did not stop Usher Raymond from changing Tameka Foster’s name to Tameka Foster-Raymond on August 3, 2007. After announcing their engagement in February of the same year, the couple exchanged vows at a ceremony held in Atlanta. That November, Usher became a father for the first time.
Entering into marriage with Tameka Foster stapled Usher as the stepfather to her three sons from relationships that preceded the singer. But on November 26, 2007, Usher Raymond V was born. A joyous Usher shared via statement at the time that the parents were “proud of our beautiful son” and called him a “blessing.” A few months later, however, reports began to circulate that there was trouble in the Raymond household and they were on the way to a divorce. But Usher would go on TRL to debunk the rumor, passionately proclaiming that the rumors were not true. He also exclaimed that he was tired of the “trash” talk surrounding their relationship.
Usher became a father again later that year on December 10 to Naveid Ely Raymond. But the relationship between the two would not last and in 2009, Usher filed for a divorce. Usher was later granted primary custory of their children. Tragedy then struck years later while their very public custody dispute was raging on when Foster’s son Kile Glover became severely injured following a jet-ski accident. Glover would later succumb to his injuries.
Usher then quietly married his longtime girlfriend Grace Miguel in 2015. But their union would be cut short after three years of marriage. According to a report by The Jasmine Brand, the couple had been “fighting non-stop” for some time and sources reveal that the reason for their split was due to Miguel wanting more children. She already had two children from a previous relationship. Usher reportedly was against the idea, causing a “serious strain” on their relationship.
In a turn of events, Usher began to date music executive Jenn Goicoechea in 2019 and seemingly had a change of heart. Because in September of 2020, Usher became a father once again. They say that the third time’s the charm, and this proved to be true for Usher as he was now the father to a baby girl named Sovereign Bo Raymond. A year later, the singer and Goicoechea welcomed the newest member of the Raymond clan, and his FOURTH child! Sire Castrello Raymond was born “at 6:42pm weighing 7lbs 13oz,” according the singer’s Instagram page. We wish the best for the Raymonds!