like trying to nail Jell-O to the wall

like trying to nail Jell-O to the wall

Incredibly difficult or impossible, such that it could be seen as a foolish or worthless endeavor to attempt. (Jell-O is a brand of gelatin-based deserts, which are known for being wobbly and unstable.) Trying to have a reasonable debate with her father is like trying to nail Jell-O to the wall. If they can't secure a victory here, climbing back to spot in the finals will be like trying to nail Jell-O to the wall.
See also: like, nail, trying, wall

like trying to nail Jell-O to the wall

AMERICAN
If something is like trying to nail Jell-O to the wall, it is impossible or extremely difficult. Jell-O is a trademark. Trying to describe the party's policy on this is like trying to nail Jell-O to the wall. Note: Jell-O is a dessert that resembles ready-made jelly. This expression was first used by the American President Theodore Roosevelt in a letter to William Roscoe Thayer in 1915. He was describing the difficulty of negotiating with Colombia over the Panama Canal.
See also: like, nail, trying, wall
References in classic literature ?
That rich undulating district of Loamshire to which Hayslope belonged lies close to a grim outskirt of Stonyshire, overlooked by its barren hills as a pretty blooming sister may sometimes be seen linked in the arm of a rugged, tall, swarthy brother; and in two or three hours' ride the traveller might exchange a bleak treeless region, intersected by lines of cold grey stone, for one where his road wound under the shelter of woods, or up swelling hills, muffled with hedgerows and long meadow-grass and thick corn; and where at every turn he came upon some fine old country-seat nestled in the valley or crowning the slope, some homestead with its long length of barn and its cluster of golden ricks, some grey steeple looking out from a pretty confusion of trees and thatch and dark-red tiles.
And reining in popular culture - or, more precisely, the meaning of a particular piece of pop culture - is like trying to nail Jell-O to the wall.
In such an apathetic organization, instituting change is like trying to nail Jell-O to the wall.