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Like nailing jello to a cat.

The ultimate in complexity and difficulty. This is a combination of two other analogies:

- Like herding cats
- Like nailing jello to a tree
"Getting the House of Representatives to agree on a topic is like nailing jello to a cat."
Related Words

like the Wild Man of Borneo 

wildly messy

(said of a persons appearence)
"You look look the Wild Man of Borneo."

Like for a like 

A Facebook status update frequently seen when someone is extremely bored, and involves them replying to any likes on the post by typing a positive comment on that person's wall. It can become quite forced when the person who likes the post isn't well liked or well known by the poster of the status update. It also helps boost the ego of people who like the post as they are always complimented.
Alvin: Like for a like

Jason likes the post.
Alvin posts on Jason's wall: I've known you for ages and we've been on the same soccer team together.

Like-arrhea

Medical condition characterized by frequent and excessive use of the word "like". Common in teenage girls.
Teenage girl: "So, like, I, like, told her, like, whatever. Like."

Like a Fox

"Like a Fox" is used after an action that one has just achieved as a discriptive phrase. When you have done something, adding "Like a Fox!" at the end will emphisize the slyness, talent or precision you or someone else has achieved something. "Like a Fox" can also be said; "Like Fox!". Like a Fox is traced back as far as an ancient phanton comic, where the Phantom states; "Crazy like a fox"
"I tricked you Like a Fox!"
"I am smart Likke Fox!"
"Stupid like a fox!" -Homer
Like a Fox by Mark November 14, 2004

like nailing jello to a tree 

It is said that nailing jello to a tree is impossible, therefor something that is like 'nailing jello to a tree' is something you just can't do.
Convincing that popular hunk of spunk to take me to the prom would be like nailing jello to a tree.