Willow Smith and De'Wayne Jackson were first linked to one another in October 2021. According to an Instagram post shared by Jackson that month, he was on tour with Smith as she traveled around the world for her 2021 Life Tour. De'Wayne had dropped his debut album, "Stains," earlier that year, so the timing was perfect for them to tour together. The talented twosome even shared matching pictures of themselves backstage during one concert. Willow captioned her animated photo with "Black Rockstars." While neither rockstar officially confirmed they were dating at the time, it wouldn't be long before fans knew for sure that something was going on between the two.
Things would warm up between Jackson and Smith a few months later. In December, the two musicians were photographed on a Miami beach together, and they looked very much like a couple in love (via Daily Mail). They weren't shy about PDA — the lovebirds were captured cuddling and sharing kisses as they stretched out on a pair of lounge chairs. They were also seen applying sunscreen to one another and sharing cold drinks.
The "Whip My Hair" singer and her rumored beau were in town for the Playboy x Big Bunny event that month, so they were probably taking a little time to enjoy the sunny beaches that Miami is famous for while they were in the area.
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