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Amidst the buzz of celebrity gossip and media scrutiny, the year 2009 marked a notable moment of speculation surrounding Usher's sexuality. However, one particular question lingered prominently in 2009 — was Usher gay? The musician's ex-wife's friend stated otherwise.
Usher, born Usher Terry Raymond IV, is not shy to bare his soul, making a literal song and dance about his past infidelities in his 2004 album "Confessions." However, two short-lived marriages mark his dating history, and he has four children with different mothers.
Several lawsuits have been waged against the artist, with the people involved claiming he gave them a sexually transmitted disease. He is currently in a relationship with the mother of his two youngest children for over seven years.

Tamika Foster and Usher at the 61st Annual Tony Awards on June 10, 2007. | Source: Getty Images
In mid-2009, a few weeks after Usher filed for divorce from his wife of almost two years, Tameka Foster, the stylist's best friend Nyeisha Dewitt, slammed claims that Tameka was a gold digger. On rumors about the singer's sexuality, she said:
"No way — I believe unequivocally that he is a straight man. That's never been an issue."
Nyeisha said that Tameka was "blindsided" when Usher filed for divorce on June 12, months after she gave birth to their second son Naviyd Ely Raymond. They married in August 2007 and had Usher "Cinco" Raymond V that November.

Chilli and Usher during EMI Grammy at The Blue Fin in New York City, New York. | Source: Getty Images
Usher was Chilli Thomas from TLC's first "adult love." The duo dated between 2001 and 2003, attending many award shows and parties together. The timing of "Confessions," an album he released after their breakup, was about infidelity and ignited rumors that it was about them.
Usher organized a date on stage during a show in Vegas.
Chilli seemed to confirm this when she said in a radio interview that he falsely presented himself as an honest man. She swore off ever dating him again. In 2013, she denied that the album was about them, saying the liaison had run its course.

Usher and Grace Miguel at the 2017 Make a Wish Gala on November 9, 2017, in Los Angeles, California. | Source: Getty Images
Grace Miguel and Usher got together before his divorce from Tameka was finalized. They had a low-key wedding in Cuba in September 2015, which he discussed on Ellen DeGeneres' show. They announced their amicable split in March 2018.
Jenn Goicoechea, senior VP of A&R at Epic Records, knew Usher for a few years before they started dating. She posted a photo of her whispering in his ear in March 2016. They were snapped kissing in June 2019 at a producer's party.
The couple welcomed their daughter Sovereign Bo on September 24, 2000, and their son Sire Castrello on September 29, 2021. As a birthday surprise in 2022, Usher organized a date on stage during a show in Vegas with the audience watching.

Jenn Goicoechea and Usher in the front row of the Balmain Fall/Winter show at Paris Fashion Week, on February 28, 2020 | Source: Getty Images
A man claimed in a 2017 suit that Usher had not disclosed that he had genital herpes when they had intercourse at a spa in Koreatown, Los Angeles. Two women, who were plaintiffs in the lawsuit, asserted that they, too, contracted an STD from the star.
Zia Modabber, Usher's legal representation, said, "Usher will defend himself vigorously in court against these opportunistic claims, and we will not comment further on private legal matters."
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