Jack, who is also a professional comedian, has hosted the Royal Variety Performance several times and one year the Duke and Duchess of Cambridge were sitting in the royal box. The Fresh Meat star thought it might be a good opportunity to bring up the fact that he and Kate attended the same exclusive private school Marlborough College. However, as Kate is six years his senior, they never spoke while they were at school.
That said, he insisted that the Duchess was his “first crush”.
Jack said at the 2014 show: “We were actually at school together. This is true. We were at the same school.
“I was a bit younger than you, but this is the first time I’ve seen you since school, so hello.
“I don’t know whether it’s appropriate given the circumstances, but you were probably my first ever crush.
Prince William reportedly made a passive-aggressive comment after Jack Whitehall flirted with Kate
Actor and comedian Jack Whitehall joked about fancying Kate
“Okay, definitely inappropriate. You Highness is giving me a very sharp look.”
Jack did not get away with his on-stage flirting, however, and earned himself an awkward conversation with William afterwards.
He revealed on The Jonathan Ross Show that he met William after the show, who called him out on his comments.
He told TV chat show host Jonathan Ross: “I flirted a little because I said she was one of my first crushes at school.
TV chat show host Jonathan Ross
“And then in the line-up William came over and he was very funny.
“Because he was very nice, but very passive-aggressive, ‘Oh so you were flirting with my missus? Oh no, no, that was very, very funny’.
“That’s him going, ‘I could have you beheaded.’”
He also admitted that, despite branding her as “the one that got away”, he never had a chance with the beautiful Kate.
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Jack recalled meeting the royals on The Jonathan Ross Show
He said: “She was a lot older than me. She was in sixth form ‒ it was never going to happen, I was in a head brace!”
Jack also described how he was standing next to American singer Demi Lovato in the line-up at the Royal Variety Show, who did not seem to understand his British humour.
He explained how everyone is always very nervous with the line-ups and Demi asked him what the protocol was with the “royal bump”, as Kate had been pregnant with Princess Charlotte at the time.
Demi wanted to know whether it was considered acceptable to talk about the baby.
Jack joked: “The Duchess of Cambridge, I think, would be offended if you don’t have a little feel.”
However, Demi reportedly took this “at face value”, not realising it was a joke.
Jack said: “As Kate Middleton’s coming along the line, I suddenly realise that we’ve got a situation here where either I need to step in and tell her and look like a complete d*** or potentially Demi Lovato from Frozen is about to get taken out by a police marksman.”
This was not the first time Jack had made jokes about the Royal Family however, as he was first part of the Royal Variety Performance in 2010.
American singer Demi Lovato
Prince Charles and Camilla were in attendance that year and Jack noted that the Royal Family were considering selling some land to help out the country in times of austerity.
He said: “Even the Royal Family are doing their bit, aren’t they?
“Last year, I watched the Queen’s speech, I watch it every year, and in it the Queen said that even the Royal Family ‘we’re making some really big cuts this year and we’re even considering selling some land’.
“I thought that is a brilliant gesture. I also thought, though, someone really needs to tell the Queen about Cash for Gold. Sorted! Kerching!”
He also joked about the difficulties of living with your parents, because you never know when they’re in the house.
He added that Charles was lucky to have an “early warning system” because the flag is always raised at Buckingham Palace when the Queen is in.