Usher serenades Kim Kardashian in Las Vegas - is he single? A look at the singer’s relationship history

My question is, when Kim Kardashian purchased the ‘ultimate on stage experience’ VIP seating tickets for an Usher concert for her birthday, did she know this package would include an impromptu serenade from the ‘Yeah’ singer?

Six months after weather conditions derailed the SKIMs CEO’s original plans to attend an Usher concert in Vegas, Kim K was seen at the Park MGM’s theatre with her friend Chris Appleton and his alleged fiancé Lukas Gage on Saturday.

Posting to her 473.2 million followers on Instagram, Kim said: “OMG! The Usher concert is fire...Finally made it to see Usher but my girls are mad that they aren’t here so I just have to come back with them ASAP.”

Seen in a tight leather corseted dress and matching choker, Kim danced as Usher approached her and her friends and serenaded the Kardashian producer-star saying ‘What up Kim, finally made it.’

As the 8-time Grammy award winning R&B singer continues his Vegas residency, which runs until 28 October, and sings to Kim K, PeopleWorld takes a look at Usher’s rollercoaster relationship history that includes a lengthy custody battle and cheating allegations:

When Usher first burst onto the R&B scene in 1994, it is thought he briefly dated fellow singer Brandy Norwood in the late 1990s. 

Despite no official confirmation of Brandy and Usher’s relationship, the pair did appear on an ‘unofficial’ duet of Brandy’s hit song ‘Who Is She 2 U’ when Usher re-recorded parts prior to its release with Atlantic Records. 

This was not the first romantic connection between Usher and a high-profile female musician as the ‘DJ Got Us Fallin in Love’ crooner made headlines with his two-year romance with TLC member Rozonda ‘Chilli’ Thomas from 2001 to 2003. 

The pair went their separate ways shortly before Usher’s fourth album ‘Confessions’ was released, which in turn sparked rumours of infidelity on Usher’s side in conjunction with Chilli stating in an interview that Usher ‘portrayed himself to be this honest and great guy, and he really wasn’t.’ A decade later, Chilli set the record straight that their break-up was a lot less dramatic than rumours suggested.

After Chilli and Usher called it quits, the Grammy winner was linked to Naomi Campbell for a few months in 2004 before he began seeing his personal stylist Tameka Foster in November 2005.

Although Usher reportedly got ‘cosy’ with Pamela Anderson in 2006, the singer’s relationship with Tameka turned into a two-year marriage when the pair tied the knot in 2007 and welcomed two sons, namely Usher ‘Cinco’ and Naviyd Ely, before entering a custody battle that lasted longer than their marriage.

While Usher was fighting for custody of his sons (which he eventually won in 2012 after the death of Tameka’s other son Kile in a tubing accident), he started to quietly date and ultimately marry his manager Grace Miguel in a surprise wedding in Cuba, 2015.

Questions arose once again surrounding Usher’s infidelity during his marriage after he was seen commenting on Victoria Secret model Jessica White’s birthday post with an aubergine emoji, however when Usher and Grace split in 2018 the pair stated:

“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 that we have for each other will only increase as we move forward."

Most recently, Usher has been in a relationship with music executive Jenn Goicoechea, welcoming his third and fourth children with her in 2020 and 2021 respectively.