Who Has Usher Dated?

R&B icon and megastar Usher has been a heartthrob for decades. Evidently, this has also proven true in his love life, as he’s had many high-profile relationships over the years. Not only has he captivated the world with his musical talents, but he’s also stirred up significant media attention for his romances. Usher’s dating history has been up for public discussion since the late '90s. Let's take a closer look at some key relationships in the life of the musical luminary, from his memorable love story with TLC’s Chilli to his more discreet love stories. 

In the late '90s, Brandy found herself amidst swirling dating rumors with Usher. Sparked by their connection within the music industry, dating speculations arose among fans. Their romance reportedly spanned a few months and remained a topic of intrigue for a few more. Despite being seen frequently together during that period, neither Usher nor Brandy chose to neither confirm nor deny the rumors surrounding their potential romantic entanglement. 

Usher and Chilli’s longtime relationship remains the most high-profile one for both stars. The two R&B hitmakers began dating in 2001 and quickly became one of the industry’s power couples. Their high-profile romance was the talk of the town, and they were inseparable. However, like many celebrity relationships, theirs faced its share of challenges, leading to a breakup in 2004. Despite parting ways, Usher and Chilli have maintained a friendship over the years. Furthermore, they always speak fondly of each other in interviews.

The R&B sensation first met this American businesswoman and model in 2002. This was during the rapid rise of his career in the music industry. While they chose to keep their relationship discreet, glimpses of the couple were occasionally caught at events and gatherings. Despite the initial connection, their romance gradually lost its spark. By 2003, the couple went their separate ways. 

In 2004, Usher entered a romantic relationship with actress and former fashion model Joy Bryant. Their connection blossomed on the set of In The Mix, a crime-comedic romance film that served as the start of their relationship. Usher even featured her in his 20-minute musical mini-movie, Caught Up. Despite a promising beginning, their journey proved to be ephemeral, and after a few months of dating, they chose different paths. 

Naomi Campbell and Usher crossed paths in 2004. Subsequently, their whirlwind romance quickly became a beloved feature in Hollywood tabloids. Beyond their success as a British supermodel and a renowned musical artist, Naomi and Usher showcased a personal chemistry that resonated both on and off the red carpet. Regrettably, their relationship was fleeting, lasting for about a few months before the duo decided to part ways. 

Usher’s romantic relationship with Karrine Stefans, the former video vixen and author, became a focal point of media attention. They initially met in 2000 and had a brief encounter, but their relationship did not last long. This was as a result of Usher subsequently falling in love with Chilli. Steffans released her book Confessions of a Video Vixen, detailing her relationship with the R&B singer. 

Usher’s relationship with stylist and wardrobe consultant Tameka Foster stirred significant controversy. The couple’s romance led to an engagement in 2007 and a private wedding ceremony later that year. However, the union faced intense scrutiny from the media and fans. Despite the challenges, Usher and Tameka birthed two sons: Usher “Cinco” Raymond V and Naviyd Ely. The relationship ultimately ended in a highly publicized divorce in 2009. 

Usher and Grace Miguel, a well-respected music executive, first met in 2009 when he was still undergoing his separation from Tameka. The couple kept their friendship-turned-relationship relatively private until they got engaged and married in 2015. While they were together, Grace became Usher’s manager. In 2018, Usher and Grace announced their separation, with Usher later filing for divorce. The two remained discreet about the reasons behind their split, choosing to separate amicably. 

In 2019, Usher fell in love with Jenn Goicoechea, a music executive. Before publicly acknowledging their relationship, the couple had been seen together at numerous events and festivals. Their love flourished, culminating in the arrival of their daughter, Sovereign Bo Raymond, in September 2020. The couple also welcomed another boy, Sire Castrello Raymond, in 2021.

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