Jack Whitehall is known for his slightly awkward, British style of humour, which often sees him cracking self-deprecating jokes and making those around him feel uncomfortable.
But as he hosted the BRIT Awards last night, the comedian managed to get himself into a particularly bad pickle when he made a weird quip about Harry Styles and his sister Gemma.
Whitehall went out into the audience and seated himself next to former One Direction singer Harry Styles.
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After a bit of banter with Lizzo, who was sat right behind them, Whitehall turned to the two women seated next to Styles and asked: "I don't want to pry, have you brought someone here with you tonight?
"Is one of these ladies your date?"
Styles pointed to the brunette to his right and said with a straight face: "That's my sister."
An embarrassed Whitehall quickly replied: "Sister? Oh God, sorry!"
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As Styles' sister took a swig of Champagne, Whitehall carried on with his patter, in turn making things even more awkward.
Worried that his apologies came across as an insult to Gemma, he said: "No, no - that's great! Keep it in the family... Not keep it in the family, I meant... It's nice to bring your family. I brought my mum! I brought my mum with me!"
As Gemma - a writer, who also happens to have 5.1 million followers on Instagram - turned away, rolling her eyes, her brother leant into the microphone and calmly asked Whitehall: "How is Hilary?"
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As Whitehall explained his mum Hilary was 'over there, probably throwing herself at Rod Stewart,' Styles leapt up to wave in her direction like the polite young man he is.
Earlier in their chat, Whitehall took a moment to reflect on how well Styles had done since his early days in The X-Factor, which he joked was 'like three Simon Cowell faces ago'.
He said: "Back then I think if you told people that you were going to be writing these critically-acclaimed albums, some people might be surprised.
"How cool is it that your solo stuff is being taken so seriously?"
After a pregnant pause, Styles replied: "Did you not take me seriously, Jack?"
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"No, I've always taken you seriously! Up All Night, that is my Sergeant Pepper, my friend. I've always respected you - as a solo artist and in One Direction!"
All-in-all, there were clearly no hard feelings from the evening, and it looks like Whitehall and Styles (OK, and Lizzo) had a lot of fun together.
Taking to Twitter after the show, Whitehall said: "Favourite Brits ever. Rod and Harry fighting over my mum, Queen Lizzo, Scottish Beyoncé being a legend, Dave! Some of the best performances I've ever seen. Massive team of people make that show happen, well done to all of them! #BritAwards2020."
In another tweet, he added: "New show. Me @lizzo and @Harry_Styles travelling round the world in a camper van."
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Netflix, which streams Whitehall's series Travels With My Father, replied: "OK, but you're breaking it to your dad."
Featured Image Credit: BRITs/YouTube
Topics: Entertainment, Celebrity