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Awkward Moment King Charles Was ‘Headbutted’ by Girlfriend While Trying to Kiss Her

Turns out, dating the future king came with its own share of royal protocol and an awkward headbutt!

King Charles following an event at the Kosovo Assembly building. (Cover Image Source: Getty Images | John Stillwell/Pool)
King Charles following an event at the Kosovo Assembly building. (Cover Image Source: Getty Images | John Stillwell/Pool)

Following royal protocol is harder than it looks, especially with endless rules to remember. Just ask one of King Charles’s former girlfriends, who accidentally headbutted him while trying to curtsey. Royal author Catherine Mayer recalled the awkward behind-the-scenes moment, revealing that while the girlfriend was supposed to formally address Charles as "Sir" followed by a curtsy, the carefully choreographed moment took a hilariously painful turn when their heads collided.

King Charles is kissed by an elderly woman outside Cwmaman Public Hall and Institute. (Image Source: Getty Images| Tim Graham Picture Library)
King Charles is kissed by an elderly woman outside Cwmaman Public Hall and Institute. (Image Source: Getty Images | Tim Graham Picture Library)

Speaking on HELLO!'s A Right Royal Podcast, Mayer claimed that even Charles's partners were expected to follow protocol even when no one was watching. She explained that she was "lucky enough to see royals behind closed doors" and assumed that they "kind of kick off protocol along with their shoes" behind the cameras, but that was far from the case. She added, "I talked to one of Charles's old girlfriends, who was there for the biography I wrote of him, and she told me this really funny story about how they were all in this room waiting for him to come, and you know they were all smoking out the windows, and you know, being young people."

Britain's King Charles III gestures as he sits with Nigeria's President Bola Tinubu (obscured) inside the Australian State Coach following a formal welcome at Datchet Road, on the first day of State Visit by The President of the Federal Republic of Nigeria on March 18, 2026 in Windsor, England. (Photo by Justin Tallis - Pool/Getty Images)
King Charles, following a formal welcome at Datchet Road. (Image Source: Getty Images | Justin Tallis/Pool)

Further reflecting on the event, she said that as soon as the then-Prince Charles had arrived in the room, the people were expected to call him 'Sir,' and "she [the girlfriend] was supposed to curtsy to him [Charles] and call him 'Sir' whenever she met him, even though she was like his girlfriend. So she goes to curtsy just as he leans forward to kiss her. He leans forward to kiss her, and she gives him a Glasgow kiss." For the unversed, in British slang, a 'Glasgow kiss' is a playful term for a headbutt, whether it happens on purpose or by mistake.

King Charles III attends the dedication ceremony for a new memorial to the Armed Forces LGBT+ community at the National Memorial Arboretum on October 27, 2025 in Alrewas, Staffordshire. (Photo by Max Mumby/Indigo/Getty Images)
King Charles attends the dedication ceremony at the National Memorial Arboretum. (Image Source: Getty Images | Max Mumby/Indigo)

While the woman in Mayer's account is unnamed, it is alleged that the King dated close to 20 women before marrying the late Princess Diana. Many of them were from Britain's aristocratic families and were nicknamed 'Charlie's Angels' by the UK press. One of his earliest relationships was with Lucia Santa Cruz, whom he met while studying at Trinity College. Often described by royal biographers as his 'first serious love,' Lucia is also widely believed to have introduced Charles to the now Queen Camilla. Over the years, the King was also romantically linked to Davina Sheffield, Lady Jane Wellesley, Lady Amanda Knatchbull, Sabrina Guinness, and Lady Sarah Spencer, who was his late wife's sister.

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