Tom Holland's Daring Cross-Dressing Performance Was a 'Turning Point' for Zendaya, Source Says: 'It Really Resonated With Her'

Zendaya is said to have developed an unexpected fascination after watching Tom Holland's now-famous Rihanna lip-sync routine – a moment insiders now tell OK! marked the beginning of her romantic interest in the actor.

The actress, 29, and Holland, 30, first met while filming Spider-Man: Homecoming in 2016, later appearing together on Lip Sync Battle in 2017 to promote the film.

During the show, Holland performed a highly stylized routine to Rihanna's "Umbrella," dressed in a black vinyl corset and shorts inspired by the singer's original music video.

Zendaya, who performed her own routines to Bruno Mars' "24K Magic" and Erykah Badu's "Tyrone," watched from the side of the stage as the performance unfolded.

At the time, the pair was not publicly linked, with their relationship confirmed years later in 2021 after they were photographed kissing.

A source close to the production told us: "That performance was a real turning point for Zendaya – she was completely taken aback, and you could see how quickly it drew her in. It was not simply that it was entertaining or playful – it highlighted just how fearless and versatile Tom is as a performer, which left a strong impression on her. There was an initial moment of disbelief, almost like she could not quite process what she was seeing, but that feeling very quickly shifted into genuine respect and fascination. It exposed a side of him that went far beyond what people assumed, and that unexpected depth is what really resonated with her."

The performance quickly went viral, with Holland's willingness to embrace the role of the character widely praised.

Another source said: "For a male actor to embrace something so bold and unconventional on such a public stage requires a huge amount of self-assurance, and Tom did not hesitate – he committed to it completely. That level of fearlessness is exactly what caught Zendaya's attention and made it so compelling for her to watch."

The same source described Holland at the time as "not immediately striking in a traditional, leading-man way," adding: "He might not fit the classic mold at first glance, but what he brings in terms of ability, presence, and sheer charm more than compensates – that is what truly sets him apart."

Zendaya's reaction during the broadcast of Holland's cross-dressing performance – laughing before appearing visibly impressed – has since been repeatedly cited by fans as an early indicator of their chemistry.

"You can almost pinpoint the exact moment her reaction changes – there is an initial flash of surprise, like she did not quite expect what she was seeing, and then it softens into genuine admiration," our source said. "It is a very visible shift, and one that feels significant when you look back on it. Moments like that tend to stay with people, and it is easy to imagine it becoming something they look back on together for years to come."

Holland and Zendaya's relationship has evolved significantly since the lip-syncing appearance.

Earlier this year, Zendaya's stylist, Law Roach, sparked speculation the pair had secretly married by suggesting the couple had already got hitched.

Speaking on a red carpet in Los Angeles on March 1, Roach said: "The wedding has already happened. You missed it."

When pressed, he added: "It's very true!"

Holland later confirmed the marriage in June during an interview with Esquire, prompted by confusion among family members over circulating AI-generated wedding images.

He said: "No, because they were all there," referring to whether relatives believed they had missed the ceremony.

However, he declined to provide further details, adding: "That's all you'll get on that."

The couple, who became engaged in September 2025 when Holland referred to Zendaya as his "fiancée" during a public panel, have consistently maintained a privacy preference.

Holland, who stars in The Odyssey alongside Zendaya, has previously indicated a reluctance to discuss their relationship publicly, emphasizing the importance of keeping personal matters out of the spotlight.

Their connection, however, continues to attract huge attention, with the Lip Sync Battle performance frequently revisited as a defining early moment in their romance.