conundrum
Meaning: puzzle, problem
Usage: Interpreting Jane’s behavior was a constant conundrum.
inextricable
Meaning: hopelessly tangled or entangled
Usage: Unless I look at the solution manual, I have no way of solving this inextricable problem.
morass
Meaning: a wet swampy bog; figuratively, something that traps and confuses
Usage: When Theresa lost her job, she could not get out of her financial morass.
quagmire
Meaning: a difficult situation
Usage: The committee fell into a quagmire when every proposed solution created a new problem.
quandary
Meaning: a perplexed, unresolvable state
Usage: Carlos found himself in a quandary: should he choose mint chocolate chip or cookie dough?