King Charles
When it comes to cringe, look no further than the newly appointed King Charles.
Back when he was still just a mere prince, the royal Casanova was revealed to get quite, erm, creative when it came to wooing his mistress (now Queen Consort), Camilla Parker-Bowles. In 1993, an intimate and shockingly explicit (at least for the English) phone transcription from 1989 was printed by the British tabloids, in which Charles memorably mentions "living inside [her] trousers" and being resurrected as her "Tampax."
While it technically went down in a time before "sexting," the conversation henceforth known as "Tampongate" has lived on in infamy for decades.
Alas, at least the two-timing couple finally got their happy ending together.
[Screenshot via Esquire]
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