In tonight's instalment of Jack's A League of Their Own: US Road Trip 2.0, the Fresh Meat star gets an awkward surprise when the football ace and former cricket captain decide to pull a hilarious practical joke on him.
Jamie, 43, is shocked when he discovers that the 28-year-old comedian has several A-list numbers in his phone, and sets about stealing it while Jack is sleeping.
He then messages Orlando, 40, a seriously racy message about the infamous naked pictures that emerged of the Hollywood actor on holiday last year.
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Jack Whitehall received a very racy text from Orlando Bloom
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Along with Freddie, 39, he writes: "Just seen these pics of your c***. You're really packing some heat. Great to see a man happy to let it all hang out. Proud of you brother. In LA, would love to check it out."
When Jack wakes up he is understandably angry and embarrassed, telling his road trip buddies: "I've only met Orlando Bloom once and I barely know him.
"The only message I've ever sent him is about his c*** and he's going to think I am so weird."
Jamie Redknapp steals Jack's phone to send a saucy text to Orlando
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Freddie Flintoff was in hysterics at Orlando's response
However, luckily, Orlando seems to find the whole situation hilarious, messaging back with a naughty proposition.
"I'm shooting in Shanghai for the next two months," he says. "If you want to check out this c***, you'd better come to China."
Freddie and Jamie burst out laughing at the hysterical response, while Jack simply calls them both "d***s".
A League of Their Own: US Road Trip 2.0 airs tonight at 9pm on Sky 1.