In the late 1970s, Prince Charles first met his future bride, Lady Diana Spencer, when she was still a teenager and the prince was dating her older sister, Sarah Spencer, according to Insider. The prince was dating Diana’s sister as an attempt to move on from his ex-girlfriend (and now-wife) Camilla Parker Bowles, whom he’d been seeing for multiple years prior to being introduced to Diana. Of course, their relationship didn’t last, as Time reported that Sarah once told Woman’s Own she couldn’t see a future with Prince Charles, saying she “wouldn’t marry anyone I didn’t love whether he were the dustman or the King of England,” once again leaving Charles a royal bachelor.
Prince Charles has opened up about first meeting Princess Diana when she only 16 years old in 1977, remembering the future People’s Princess as “very jolly and amusing and attractive” — but the initial reaction wasn’t reciprocated.
Princess Diana recalled thinking the prince was a “sad man” and being “so unimpressed” the times she encountered him as a teenager. It wasn’t until nearly two years after Prince Charles’ relationship with Princess Diana’s older sister had swiftly come to an end that the pair reconnected in light of a tragic event and began their legendary romance.