Though they may be most commonly depicted in brawling couples on this website, the Royal Family is not above a good extramarital affair. Alongside King Henry VIII’s four mistresses — there’s a reason why Protestantism exists — this two-timing isn’t reserved for Tudor times. In 1994, King Charles III got candid about his marital woes to his then-estranged wife, Princess Diana, admitting that he had stepped out on her. "Yes ... Until it became irretrievably broken down, us both having tried,” he said when reporter Jonathan Dimbleby asked him if he had remained faithful to his soon-to-be ex back in 1994.

We’ve all associated with questionable people in our days — who hasn’t bought cigarettes from that community college kid outside your high school? — yet Prince Andrew’s friendship with Jeffrey Epstein takes it to another level. Alongside allegedly spending “weeks” at the late financier’s home, it appears Andrew may have picked up a few of his pal’s alarming habits. In 2022, Prince Andrew reached a settlement with whistleblower Virginia Giuffre, who alleged she was forced to have sex with the royal as a teen after being trafficked by Epstein.

This one is pretty self-explanatory. Don't dress up like a Nazi, even on Halloween.

And it’s not just King Charles III getting in on the fun. Prince William may have married Kate Middleton in 2011 FC but according to some rumors, he’s gotten it on outside of his royal marriage, some speculating that he hooked up with longtime pal, Rose Hanbury. But even as the rumor mill churns, royal expert Omid Scobie is doubtful that the newly-minted Duke of Wales FC actually two-timed his definitely-not-missing wife. “Unfortunately, if a rumor’s left to kind of do its own thing, it can run 20 laps around the world before you even think about what, how you want to kind of address it,” he said of the whispers back in November 2023, noting that even though “there’s no truth to suggest that they are true,” they won’t die sans a palace denial. But hey, who knows: A side-relationship that’s probably a lot easier sans as his wife recovers from her massive BBL abdominal surgery.