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The two spent New Years together in Dubai, and Khadra, who recently debuted his new single "Love It," was seen snapping photos of the blonde stunner from the front rows of fashion week.
Despite the couple's magazine features, and their many red carpet appearances, the model and rapper called off their engagement after being together for a year and a half, in 2014 citing busy schedules getting in the way.
The pair, who has been reportedly dating since early 2015, made their first red carpet appearance together at the 2016 Grammy Awards—seems like things are getting serious.
Windsor has been linked to Khadra, an old friend of fellow IMG Model Gigi Hadid, since 2014.