Prince Charles has a reputation for being a womanizer, dating over 20 women before marrying Princess Diana in 1981, including Diana's sister, Sarah Spencer. On paper, Charles and Diana seemed to be a wonderful match, but they were considerably less compatible than they initially anticipated.

Charles described Diana as "very merry, humorous, and lovely" when she was just 16, and they began dating a few years later in 1980. Diana must have found Charles entertaining as well, as the two announced their engagement after only 12 dates.

There was always speculation that Prince Charles was having an affair with Camilla Parker-Bowles, who is now his wife. Princess Diana discovered a gold bracelet intended for Camilla just two days before their wedding and confronted Prince Charles, but he gave it to Camilla nevertheless.

It's surprising Princess Diana and Prince Charles were able to marry, seeing as how there were so many red flags in their romance. Of course, it didn’t last, as Charles confirmed his affair with Camilla, and he and Diana divorced after 15 years of marriage.