Of course, we can’t discuss King Charles III’s dating history without talking about the Diana Spencer. The “People’s Princess” has a legacy that’s worth thousands of words, but when she got engaged to Charles, she was a 19-year-old kid who didn’t see it coming. As noted by Marie Claire, Charles and Diana had gone out together a total of 12 times — yes, 12 — before he asked her to marry him (via Daily Mail). The Guardian reported at the time that the then-prince was “amazed” that Diana said yes, and even Diana seemed to be completely caught off guard by the proposal.
In the documentary, “Charles and Di: The Truth Behind Their Wedding,” royal editor Ingrid Seward shed some light on the moment Charles popped the question, telling viewers that it was more awkward than intimate (via Yahoo). After taking Diana to the nursery — we’re a little weirded out by that too — Charles proposed, and Diana “burst out laughing.” “I think that was probably just her nerves,” Seward said. “She didn’t think it was the most romantic of proposals but she had the proposal.”
Much like the proposal, the couple’s relationship was not the fairytale that many believed it to be. Royal biographer Christopher Wilson later said that after Charles proposed, he called his mother, Queen Elizabeth II, and told her, “There, I’ve done it now. You’ve asked me to get married to somebody, and I’ve fixed it” (via Yahoo).
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