And when the big day arrives on 11 February, the singer is also expected to receive immense support from his fans, family, and loved ones, including his girlfriend, Jenn Goicoechea. Usher's dating history includes Usher's famous exes like Naomi Campbell, Rozonda 'Chilli' Thomas, and many more. Usher and Jennifer Goicoecheas second child together has arrived The 42-year-old singer and his girlfriend welcomed a son, Sire Castrello Raymond, on Sept. Usher is gearing up to perform at the 2024 Super Bowl Halftime show, with the high-profile event just one month away. In March 2018, Usher separated from his wife. Their chemistry was undeniable on the set of Usher’s music video. In September 2015, Usher married his long time girlfriend and manager Grace Miguel.

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