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After the untimely death of his 11-year-old step-son, Kile Glover in 2012, and his eldest son’s Usher V’s hospital scare in 2013, it seems that the heartbroken Usher finally found love with his manager, Grace Miguel.The private couple secretly wed in 2015, while on vacation in Cuba.

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Here’s Usher’s complete dating timeline: Usher began dating Rozonda Thomas in 2001, and their relationship lasted for two years. The pair seemed deeply in love, and were frequently photographed together by the paparazzi.Usher began dating the model, Eishia Brightwell in 2005 and the adorable pair went everywhere together.The paparazzi clicked pictures of the couple at several red carpet events including the Grammys, the Vanity Fair Oscar Party, and the NAACP Awards.Usher publicly announced his engagement onstage at the Spirit Awards in 2007.