Jack Whitehall once accidentally sent a photo of his rash to a university lecturer.
The 33-year-old actor and comedian developed a "rather nasty rash" on his rear when he was on vacation in Cambodia, and after contacting his doctor back in the UK, he was told to send over some snaps so he could be diagnosed.
But to Jack's horror, he made a disastrous error when he sent over the email containing the photos of his behind.
He recalled: "I fired off the email to my doctor and sat down to wait.
"An hour later and I was a wreck, imagining the worst-case scenario in my head. I've got bum cancer, is that a thing?
"Eventually, I gave in. I called him up and I said, 'Doc, put me out of my misery. What's wrong with me?'
"He goes, 'Jack, I'm still waiting for the picture.' My whole world went into soft focus, my heartbeat must have ground to a halt."
The Jungle Cruise star didn't send the pictures to his doctor, but instead emailed them to a university professor that worked at a school Jack applied to as a teenager.
He added: "To my horror, I saw that I had indeed sent the email but, in my hurry to fire it off, I had not spotted that my phone had auto-filled in the email address from a Dr Stein to a Dr Stephens.
"Dr Stephens is, in fact, a doctor of art history.
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"He is a professor at a university I had applied to some ten years ago and was rejected from.
"How bizarre a morning must he have had?"
Jack never got a response from the professor, and still has a draft email which he would have sent to apologise for the mishap.
Writing in his new book, How To Survive Family Holidays - an excerpt of which was published in The Sun newspaper - he said: "He never did respond.
"To this day, I have an email in my drafts somewhere, in which I was going to pass off the picture as a piece of abstract art that I was thinking of purchasing and wanted his opinion on."