Cressida Bonas, an actress who was Prince Harry’s last serious girlfriend before Meghan Markle, reportedly saw a future with him until “he ruined his chances” by embarrassing her.

Cressida was introduced to Harry by his cousin Princess Eugenie in 2012, and they dated for the next two years. However, something happened early on in their relationship that “humiliated” Cressida and nearly caused them to break up forever.

“Harry has blown it,” a friend of hers said at the time, according to The Express.

Cressida was deeply embarrassed when photographs of a nude Harry with a woman hiding behind him came out and quickly spread all over the world. This was referenced recently by comedian Dax Shepard when he interviewed Harry on his “Armchair Podcast.”

“I’m really excited to meet you because, in full disclosure, I’m the most ill-informed person on the Royal Family, at least in my circle,” Dax said to kick off the interview. “You’re the only one I ever knew and simply because you were in those awesome nude photos in Vegas. And I literally said to myself, ‘This guy’s a party!'”

“I’m sure you’re constantly looking for other people to sort of balance out your own behavior, right?” Harry replied, going on to explain that it happened a few weeks before he flew off to Afghanistan.

A friend of Cressida’s said at the time that the incident did not go down well with her.

“Cressida saw a future with Harry but then he went and embarrassed her like he did in Vegas,” the friend said. “He clearly isn’t as serious about her as he had claimed to be in Necker and it’s highly embarrassing. He’s ruined his chances now. She’s humiliated.”

The photos also caused a huge stir within the royal family.

“Charles said to Harry, ‘As it stands, son, it’s bearable and we can manage it, but is there any more to come out?’” a source said. “He has not been too angry so far and has advised Harry to keep his head down and let the situation calm down. It’s more his style to put his arm around Harry’s shoulder and have a word than to rollick him.”

Cressida and Harry finally broke up after she ultimately could not see herself being under the scrutiny of a royal. They remained on good enough terms, however, that she attended his wedding to Meghan in 2018.