Revelations that John Key repeatedly pulled the hair of a waitress isn't the first time the actions of our Prime Minister has made us squirm in our seats.
Comments about Maori, David Beckham, foreign leaders and a radio DJ's choice of fashion puts him close to Queen Elizabeth's husband the Duke of Edinburgh and Aussie Prime Minister Tony Abbott in a league of face-palm moments.
Some would argue this less-polished side of our leader is what makes him more likeable.
Here we have compiled a list of the times our PM has most made our skin crawl:
Describing radio DJ Jamie Mackay's outfit as 'gay'
Prime Minister John Key sparked international outcry when he insulted DJ Jamie Mackay for what he was wearing.
John Key said: "What you're wearing is an absolute disgrace. You parade yourself as some sort of center-right interested community leader and you're in the red."
"You're never going to make it. You've got that gay red top on."
He stopped short of a full apology, saying young people use it [the word gay] all the time.
It should be mentioned Key is an advocate for gay marriage, but this comment is just one of a number of blunders the PM has made.
Key describes David Beckham as thick as bats***
On the same day he made the remark about DJ Jamie Mackay, John Key made global headlines after reportedly telling students at St Hilda's Collegiate in Dunedin that Beckham was a nice guy but "thick as bats***".
The famous British footballer spent 45 minutes with Key's son Max on a visit to New Zealand in 2008.
Asked whether he really thought Beckham was dumb, Key said: "No, he's smart. He's made more money than me".
Key, who is reported to be worth about $50 million, still isn't denying he made the "thick as bats***" remark.
"All I'm saying is I'm not going to engage in what some person has reported me as saying because it may or may not be correct," he said.
Way to put NZ on the map, John.
The 'I'm with stupid' photo
Actress Chelsie Preston Crayford supposedly had her photo taken with John Key, while holding the sign 'I'm with stupid'.
The photo was posted on Instagram and Twitter, with many people taking to social media to show their appreciation of the photo.
However, John Key believes the image was altered and the words and sign added at a later date.
The PM did take the supposed photo in good humour, saying "From what I can see she has the sign pointing in the wrong direction".
Key insinuated Tuhoe Maori were cannibals
John Key apologised over a joke which has been interpreted by some as linking Tuhoe with cannibalism.
Key sparked outrage when he opened a speech by saying if he had a meal with Tuhoe he would have been on the menu.
Some Tuhoe members took that as a suggestion members of the iwi were cannibals.
Here is what he said: "As I said, the good news was that I was having dinner with Ngati Porou as opposed to their neighbouring iwi, which is Tuhoe, in which case I would have been the dinner."
It seems only John Key got the joke.
Key's Phillip Smith joke to Chilean president
John Key last year made yet another tasteless joke which landed him in hot water.
While escaped murderer and paedophile Phillip John Smith had fled the country and landed in Chile while on his way to Brazil, it was an opportunity for Key to make the situation a little more lighthearted.
Key said: "I'll just let her know [the Chilean president] there's someone who could be out there from New Zealand that you may not want to invite round for lunch."
The public took to social media questioning Key's timing on the joke, with one tweeter saying "The greatest threat to PM Key has always been Comedy John."
The good news is that Phillip John Smith has been recaptured and is well and truly behind bars.
John Key's three-way handshake fail
No words are needed for this epic but cringe-worthy Rugby World Cup handshake fail.
You had one job! One job!
Morning news break – April 23