The etymology of conundrum is quite the conundrum! Nobody really quite knows its origins, but there are some theories. The word was first attested in 1596 to denote "a pedantic person", but then that meaning died out. A few more definitions emerged throughout the seventeenth century, including "pun" and "whim". It's uncertain if any of those usages are even related to the modern meaning, which emerged as Oxford University slang in 1645. Apparently, they might have coined it as a joke: it was considered humorous at the time to create words that looked Latin but actually weren't. After that, conundrum (which was also spelled quonundrum for a while) seeped into the popular culture, and the rest is history. Other etymological theories include having conundrum actually come from Latin or being named after an order of Jesuits.
Adam Aleksic, a rising sophomore studying linguistics and government at Harvard University, has been described as the internet's sixth most famous etymologist. He also has disturbing interests in politics, vexillology, geography, board games, conlanging, and law.