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 foolish or futile to attempt. (Jell-O is a trademark for a brand of gelatin-based desserts that have a soft, gelatinous texture.) Trying to have a reasonable debate with her father is like trying to nail Jell-O to the wall. Getting the kids to behave after a big party is like trying to nail Jell-O to the wall.
See also: like, nail, trying, wall
Farlex Dictionary of Idioms.

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
Collins COBUILD Idioms Dictionary, 3rd ed.
See also:
  • like nailing Jell-O to the wall
  • give (one) up as a bad job
  • give somebody/something up as a bad job
  • put a rope to the eye of a needle
  • bark up the wrong tree
  • bark up the wrong tree, to
  • cast stones against the wind
  • a losing game
  • roast snow in a furnace
  • pour water on a duck's back
References in periodicals archive
"It's like trying to nail Jell-O to the wall," Edmonds said.
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. It's messy, difficult, and doesn't make a whole lot of sense.