15) Usher
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Usher's romantic past would seem more glamorous and complicated than anyone would imagine, considering his status as one of R&B's biggest stars. He is known for a very long-term relationship with TLC member Chilli, which brought much public media of the early 2000s to light. The singer dated several celebrities in the wake of his split.
Other stars he dated include Jennifer Lopez and Keri Hilson, actress and model Naomi Campbell, and stylist Grace Miguel, whom he married in 2015. He and Grace separated in 2018. His relationships would cross over to his music career because most of the inspirations for the songs he would make come from his romantic life, making dating life an important part of his celebrity life.
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