Definition of conundrum
1
: a riddle whose answer is or involves a pun (as in “Why didn't the lost hikers starve in the desert? Because of the sand which is there.”)
2
a : a question or problem having only a conjectural answer
… the political conundrums involved, particularly the problem of how the richer areas … can be made to subsidize the poorer. — Douglass Cater
b : an intricate and difficult problem He is faced with the conundrum of trying to find a job without having experience.