Conundrum conundrum

I am stuck and need help.  I have been rather fixated for the past day on the word “conundrum.”  It’s one of those words that I really like, and I have on occasion tried to use, but truthfully, I really can’t wrap my mind around the full meaning.  Here’s good old Webster’s words of wisdom:

1
: a riddle whose answer is or involves a pun
2
a: a question or problem having only a conjectural answer
b: an intricate and difficult problem
OK, all you readers…I got meaning 2.  It’s meaning 1, the riddle with the pun answer that kind of boggles me.  I looked “conundrum riddles” up on google, and mostly just found a lot of silly jokes with word pun answers.  Is that all there is?  It feels like it should be something more, something deeper, you know…more of a conundrum.  🙂
The best thing I found was a passage from Alice in Wonderland from Lewis Carroll:
“Why is a raven like a writing desk?”[…]

“Have you guessed the riddle yet?” the Hatter said, turning to Alice again.

“No, I give it up,” Alice replied. “What’s the answer?”

“I haven’t the slightest idea,” said the Hatter.

“Nor I,” said the March Hare.

Alice sighed wearily. “I think you might do something better with the time,” she said, “than wasting it in asking riddles that have no answers.”

So maybe that’s what the conundrum is; we can’t really figure out what it is or what it really means, and that is the perplexing part that makes it the conundrum.
If any of you are conundrum experts, please write and share your wisdom with me.  🙂   Slainte, Lisa

I welcome your thoughts...

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