Although they fell in love during L.A.’s lockdown, Winnie and Kyle called it quits temporarily. In August 2021, TMZ first reported that the couple broke up after dating for over a year. Soon after the split, Kyle got traded from the Lakers to the Washington Wizards. It’s unclear if the trade affected his and Winnie’s romance.
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During their reported time apart, the model continued working and sharing her adventures with fans as she typically does. In December 2021, Winnie and Kyle started hanging out again for the first time since the breakup speculation. The pair attended dinner at Carbone in New York City, and photographers spotted them holding hands.
Winnie also confirmed that the couple is back on track by continuing to post photos of her and Kyle. She captioned the nickname “Mr. and Mrs. Smith” in one post while sitting on her boyfriend’s lap.