Prince Harry and Meghan Markle’s “last night of freedom” came on Halloween 2016 in Toronto, just hours before news of their relationship went public. Three months earlier, a mutual friend had set them up on a blind date at Soho House in London. What followed, Harry recounts in his memoir Spare, were secret meet-ups, disguises, and a determination to “maintain the bubble.” By October, he flew to Toronto for what he called his “first proper visit” to see Meghan’s life, dogs, and beloved home, while they walked parks and ravines and stayed vigilant about being recognized.
Sensing the story was about to break, they chose to spend their final anonymous hours at an “apocalypse”-themed Halloween party at Toronto’s Soho House with Princess Eugenie, Jack Brooksbank, and friend Markus Anderson. Haunted by a past fancy-dress scandal—his 2005 Nazi-costume mistake, later described as one of his biggest errors—Harry approached the theme with care. Instead of shopping, he borrowed Tom Hardy’s Mad Max outfit: a skeleton mask and dark clothes that made him unrecognizable. Meghan wore torn black shorts, a camo top, and fishnets. Photos later shown in their Netflix docuseries capture a carefree foursome that belied their royal realities.
Inside the “loud, dark, drunk” party, Harry experienced rare anonymity. While people did double-takes at Meghan, nobody looked twice at her “dystopian date.” He later wrote that he wished he could wear that disguise every day. By dawn, however, the “apocalypse” arrived: the couple knew their romance would no longer be secret. Minutes before Harry left for the airport, he asked Meghan if she feared what came next. “Yes. No. Maybe,” she said. Harry warned: “We’re going to be haunted… but I’ll keep you safe.” Strangely, upon landing at Heathrow, speculation seemed to cool—no photos had surfaced yet.
That calm ended November 8, 2016, when Kensington Palace confirmed the relationship. In an unusually forthright statement, Harry condemned the “sexism and racism” Meghan faced and appealed for her privacy and safety. Despite the announcement, they kept a low public profile for months. Meghan spoke about being “really happy and in love” in Vanity Fair’s October 2017 issue. Their first official public appearance came in September 2017 at the Invictus Games in Toronto, where Meghan’s “Husband” shirt by friend Misha Nonoo stoked engagement rumors. Within two months, the engagement was announced, and they married at St George’s Chapel, Windsor, in May 2018.
The Halloween episode foreshadowed their break with royal convention and their insistence on privacy—reasons later cited for stepping back in 2020. Throughout, their bond with Eugenie and Jack remained strong: shared nights out before marriage, friendly moments at the King’s 2023 Coronation, visits in Los Angeles, and Eugenie’s appearances in their Netflix series. Biographers Omid Scobie and Carolyn Durand describe Harry and Eugenie as especially close—two royals navigating life at the margins of the Firm—underlining how that final, clandestine party also captured the inner circle they would keep as their world changed forever.
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