Like Nailing Jelly to a Tree Watch this on YouTube here - Tree Video - YouTube Video Meaning: Like Nailing Jelly to a Tree means to deal with a very difficult problem or a problem that cannot be solved. a foolish or worthless attempt at something. “Ha, that will be like nailing Jelly to a tree.” In America they say "to nail jello to a tree", Jell-O being a gelatin dessert that comes in fruit flavors. Origin: The origins of both these phrases actually lie in politics. Theodore Roosevelt, in 1915 wrote a letter to William Roscoe Thayer talking about the difficulty he was having negotiating with Columbia regarding the Panama Canal, it said: 'You could no more make an agreement with them than you could nail currant jelly to a wall - and the failure to nail currant jelly to a wall is not due to the nail; it is due to the currant jelly.' Example: Today we do not hear this expression as much, but if you did hear it, it would mean t...