7 Biggest flirts in history

These seven characters somehow found a way to deal with their nerves, and are among the biggest flirts in history as a result. But be careful not to follow their example too closely, because as you’ll see, these super-flirts often got themselves (and sometimes their countries!) into major trouble with their antics…

  1. King David
    1. It may seem odd to think that the Bible can give us the story of a player, but King David of Israel (c.1002-970 BCE) is just such a character. The Bible names seven women as his wives, though it is quite possible that he had more, as well as several lovers. His most famous fling was with a lady called Bathsheba. He became obsessed with her after spotting her bathing from his rooftop, and from then on was determined to be with her. She was already married to one of his generals, but this didn’t stop them from getting together. It resulted in Bathsheba falling pregnant several times with David’s children. One of these sons, Solomon, was made the heir of David’s kingdom, but not everyone was happy with this. By David’s last years, there was chaos in the land of the once wise and great king. One of his older sons, Absalom, rebelled and tried to take over the throne, kicking off a civil war in Israel. 

  2. Queen Cleopatra
    1. This famous queen (69-30BC) was actually the seventh Cleopatra to rule over Egypt. She initially ruled together with her brothers, but took the throne for herself, after making a spectacular marriage pact (agreement) with the powerful Roman leader, Julius Caesar. Cleopatra was an intelligent and confident woman, who could definitely hold her own. She enjoyed a happy marriage with Caesar until he was dramatically assassinated in 44BC. Cleopatra fled from Rome, where she and Caesar had been living with their son and focused on protecting her Egyptian kingdom. Two years later, she came face to face with Caesar’s successor, Marcus Antonius, or Mark Antony as he is more popularly known today. At their first meeting, she was dressed up as Venus, goddess of Love, and even had pageboys attending her dressed up as little Cupids! Such was Cleopatra’s glamour and wit that Mark Antony fell head over heels for her, and they later married. The couple did not have an easy life though, as they soon faced a major threat from Octavian, a Roman who claimed to be Caesar’s adopted son. Their armies were defeated by Octavian’s men. Just like his Romeo and Juliet, Shakespeare has recorded how Cleopatra and her husband tragically killed themselves when they thought all was lost. 
  3. Henry VIII
    1. Henry VIII’s (1491-1547 AD) flirtatiousness was so momentous that it actually led to him to change the state religion of England! When Henry fell in love with Anne Boleyn, a lady at his court, he was initially forbidden from doing anything about it because his first wife, Catherine of Aragon, was still alive. Henry and Catherine were both Catholics, and according to the rules of their church, divorce was not an option. Henry dramatically rebelled against the Pope and embraced the Protestant faith  - not just for himself, but for his kingdom too - so that he could be with Anne (and hopefully have a son with her, who could inherit his kingdom). Unluckily for Anne however, Henry soon got bored of her. Jumping on rumours that she had been flirting with some of his male courtiers, he ordered for her to be beheaded, so that he could move on to his third wife: Jane Seymour! Henry would marry a grand total of six wives during his lifetime, but the total number of women that he probably tried to chat up has been lost to history...

  4.  Giacomo Casanova
    1. This Italian writer and spy (1725-1798 AD) was such a legendary flirt that his name has literally come to mean being a heartbreaker! Born in Venice, he initially was educated for a career in the church. However, Casanova was far too interested in gambling and chasing girls to commit to such a serious job. Instead, he used his brains and charm to seduce women in whichever European city he visited, and then committed the stories of his escapades to his memoirs – which are today regarded as one of the most detailed existing accounts of eighteenth-century social life (if a little exaggerated in places!). He gambled wildly and took on a wide variety of jobs (violinist, clerk, magician etc.) in order to fund his extravagant lifestyle, but his dodgy behaviour landed him in prison by 1755. He made an incredible escape after a year and then spent the rest of his life on the run, working as a spy for various different aristocrats across Europe. Even James Bond can’t match up to the antics of the real-life Casanova! 
  5. Catherine the Great
    1. Catherine II (1729-1796 AD) was the longest-ruling female ruler of Russia, and her reign marked something of a golden age for the country, which is why she has been labelled ‘Catherine the Great’. She is well regarded for having been an intelligent, cultured and considerate leader. Catherine was married to the heir to the throne, but the couple did not get along. Six months after becoming emperor, Catherine’s husband, the unpopular Peter III, was toppled from his throne. Catherine managed to win over the Russian soldiers and prevent her husband from attacking her, and was soon after empowered to rule over Russia in her own right. Catherine never married again but she did have many different boyfriends over the course of her life, several of whom were prominent men in Russian and European politics. Seeing so many different guys also meant having to handle lots of break-ups, but Catherine did this in style: giving each rejected man valuable objects, land or serfs as a parting gift. The fact that she managed to remain on friendly terms with most of her exes suggests that Catherine’s “it’s not you, it’s me” approach was pretty successful!
  6. Lord Byron
    1. Lord Byron (1788-1824 AD) was a famous Romantic poet and politician – a man who had a brilliant way with words that helped him become a hit with gentlemen and ladies alike. His mum was worried sick about his obsession with romance when he was just 15! At that age, young Byron refused to go back to boarding school, all because he claimed that one Mary Chaworth had stolen his heart. His mum was having none of it and wrote, "He has no indisposition that I know of but love, desperate love, the worst of all maladies in my opinion.” Although Byron quickly became a celebrity for his brilliant poetic works, his continued antics with the ladies would land him in deep scandal as an adult. In 1812, he openly had an affair with Lady Caroline Lamb, the wife of a prominent British politician. He broke up with Caroline after a year, and went on to spark up a relationship with, and eventually marry, her cousin, Anne Isabella Milibanke. Unsurprisingly, Caroline was not very happy about this! Lord Byron died at the young age of 36, leaving a controversial legacy behind him. 
  7. Maharani Jind Kaur
    1. Maharani Jind Kaur (1817-1863 AD) was the last queen of the nineteenth-century Sikh Empire, which incorporated much of modern-day Pakistan and northern India. She has a conflicting reputation: with historians from her region saying that she was a great heroine, whilst British colonial writers have labelled as her a flirt and party girl. British political officers who spied on her activities particularly claimed that she was having an affair with her prime minister, and portrayed her as a villainous Indian version of Catherine the Great. Major-General Henry Lawrence was empowered by treaty to take over Jind Kaur’s role at the head of her government and became her main rival in a bitter power struggle. He was particularly active in making the Maharani out to be a maneater, and sought to restrict her access to important male leaders, as he argued that she would try to seduce them for political gain. We will never know for sure whether Jind Kaur was really such a big flirt, but as the saying goes, “mud sticks!” Lawrence was able to use the accusations against the queen to have her separated from her eight year old son, and to ensure that she was banished from their kingdom for life!