Meghan Markle and Prince Harry in 2024.

Karwai Tang

Prince William’s Maybe-Affair

Sarah Rose Cholmondeley (née Hanbury), the Marchioness of Cholmondeley, allegedly had an affair with the future king in 2019. Rose and Kate, formerly close friends, apparently had a falling out as a result. At the time, Palace PR worked hard to quash the rumors, while at the same time doing little to help the then newly-married Meghan Markle, who was being ripped apart by the same press. It’s even been speculated that someone in The Firm let the tabloids smear Meghan in exchange for not running the cheating allegations.

The rumor made the rounds again in 2022 after popping up in a Deux Moi blind item with an added detail: pegging. That version of the story casts William as a repeat cheater whose wife was OK with the physical aspect, but didn’t like that William and Rose had become emotionally involved during their now-over affair.

Prince Harry’s Bad Halloween Costume

By 2005, 21-year-old Prince Harry was already known as the bad boy of the family, thanks to his history with pot and alcohol. But it was still shocking to see him display incredibly poor judgment and choose, as part of his Halloween costume…a Nazi armband. After pictures of him in his outfit his the newsstands, Harry apologized immediately.

Sarah “Fergie” Ferguson’s Controversies

A longtime friend of the royal family and Princess Diana, Sarah Ferguson fell madly in love with Prince Andrew, and the pair married in 1986 after only a three-month engagement. However, his naval career kept them apart for most of the year, and after welcoming two daughters, they separated in 1992 and divorced in 1996. They’ve maintained a famously close and amicable relationship, but “Fergie” was still able to stir up a little drama that reflected not super well on the royal family.

In 1992, the Daily Mirror published photos of Ferguson on vacation with her financial advisor, John Bryan. In the pictures, the two are getting intimate, though not in the way you might think. He has her toes in his mouth. The public assumed he was “sucking” on them, though Bryan said he was just kissing them. There were other NSFW pics from the vacation, but the toes are what people remember.

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