Usher Raymond » Dating History

Historical look at Usher Raymond relationships, listed in date order.

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Karrine Steffans
Usher Raymond and Karrine Steffans unknown date
Ayesha Butler
Usher Raymond and Ayesha Butler unknown date
Stefanie Thomas
Usher Raymond and Stefanie Thomas unknown date
Jessica White
Usher Raymond and Jessica White unknown date
THE LOVELINKS OF JESSICA WHITE According to the Internet, Ms. White has been very busy romantically - true or false? RS wanted the scoop on each. USHER - (Giggles) "Such a long time ago. We hung out. Next Question." [more]
Monica Arnold
Monica and Usher Raymond January 1995
Brandy Norwood
Brandy Norwood and Usher Raymond 1998 - 1999
Rozonda 'Chilli' Thomas
Usher Raymond and Rozonda Chilli Thomas 2001 - December 2003
Usher and Rozonda "Chilli" Thomas were a match made in musical heaven, and for three years they stayed strong. They broke up just a few months before Usher released his album "Confessions," fueling rumors that the relationship ended because he cheated on her. [more]
Melinda Santiago
Usher Raymond and Melinda Santiago 2002
The romance between Usher and Melinda Santiago mostly gained attention after stories about her tattoo surfaced. Specifically, it was rumored that actor Tyrese Gibson broke up with her because he found Usher's named tattooed on her hip. [more]
Naomi Campbell
Naomi Campbell and Usher Raymond September 2004
Usher and Naomi dated for a few months, but reports about why they split have been contradictory. Apparently he said he was bored with her, but she claimed his entourage was too controlling. [more]
Eishia Brightwell
Usher Raymond and Eishia Brightwell January 2005
Usher and Eishia Brightwell made the red carpet rounds together all through 2005. They were seen at the Grammys, the Oscars and the NAACP Awards. The two weren't seen together after 2005, however, leading to reports that the relationship had ended. [more]
Tameka Foster
Usher Raymond and Tameka Foster January 2005 - November 2009
Usher announced his engagement to Tameka Foster on stage while receiving a Spirit Award. Shortly thereafter, the two announced that Tameka was pregnant. The two had two kids together, Usher Raymond V and Naviyd Raymond, before they filed for divorce. [more]
Pamela Anderson
Usher Raymond and Pamela Anderson May 2006 - 2007 RUMOR
After months of rumors that Anderson was making beautiful music with Usher in 2006, the former Playmate denied it all – although she admitted "that's a good story. Keep that one going ... he is hot." But on New Years Eve, Anderson and the 11-years-younger R&B singer looked like the ... [more]
Grace Miguel
Usher Raymond and Grace Miguel June 2009 - August 2010
Usher and Grace Miguel rumors began after they were photographed together several times while Usher was still married to Tameka Foster. The official line was that Grace and Usher were working, as Grace is an executive at Def Jam Records. [more]

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