British television mogul, Simon Cowell is no stranger to unusual fan encounters, but one particular moment stands out as the most bizarre.
He has opened up about the strangest fan request he’s ever received during an appearance on the How To Fail podcast with Elizabeth Day. According to Cowell, the encounter took place in a restaurant, when a seemingly ordinary fan interaction took a shocking turn.
“One time—this is a true story—I was in a restaurant and this guy comes up to me and said, ‘I love your show,’” Cowell recalled. “He asked for a picture and introduced me to his wife. Then, completely out of the blue, he said, ‘Would you judge us having sex?’”
At first, Cowell assumed the man was joking. But the couple was serious—and even offered to pay him.
“I went, ‘Are you winding me up?’” he said. “And they said, ‘No, we’ll pay you.’ So I asked, ‘Well, how much?’ And it was actually a lot of money—$150,000. I thought about it for a moment, but I just couldn’t do it.”
Despite the shock, Cowell said he finds interactions like that oddly enjoyable.
“I’m actually very shy,” he admitted. “I can’t do pre-parties. Making small talk with people I don’t know is the worst. But when someone comes up and starts talking about something I love—like the shows or the artists—it makes things easier.”
Cowell also shared that fame has helped him navigate his social anxiety. “It gives you something to talk about straight away,” he explained. “It helps break the ice.”
Of course, some fan requests are more familiar territory. “People used to ask me to be rude to them, especially in America,” he added, referencing his reputation as the blunt, no-nonsense judge from his American Idol days.
