Zendaya and Tom Holland's relationship reportedly began with an unexpected moment during a 2017 television appearance on the U.S. reality show Lip Sync Battle. Friends of the couple have revealed that Zendaya, now 29, was captivated by Holland’s performance, which featured the actor dressed in drag performing a rendition of Rihanna’s hit song "Umbrella."

The performance, characterized by Holland’s black leather outfit and heels, was both raunchy and confident, drawing widespread attention online. It has since been viewed more than 173 million times on YouTube. According to sources close to Zendaya, the moment marked the point when she “fell hard” for Holland, who was 30 at the time.

“They say it’s not just sexy but it shows how amazingly talented he is,” said a source. The same source noted that the courage required for a straight actor to perform in drag added to his appeal. When Holland was first cast as Spider-Man, some commentators described him as “slightly wimpy,” but friends maintain that he compensates for his stature with exceptional talent.

The couple appeared together on Lip Sync Battle in May 2017 to promote the first Spider-Man film. During Holland’s performance, Zendaya’s reaction was reportedly a mix of surprise and delight. “You can see the shock on her face but then the admiration,” the source said, adding that the clip is likely something the couple will share with their children in the future.

Last week, Zendaya confirmed the couple’s marriage by flashing a gold wedding band while attending a red carpet event for the release of their latest film, Spider-Man: Brand New Day. The confirmation ended months of speculation about their relationship status, finally revealing that the pair had quietly tied the knot.