Senator Richard Blumenthal (D-CT) uttered this gem on CNN January 4, 2019. The context is regarding the recent Government shutdown over Trump’s proposed wall. This is a conflation of “like talking to a wall” (a futile conversation because the other party is not listening) and “like nailing Jello to a wall” (a futile attempt at something). Both idioms contain the word “wall” (appropriate in context, right?) and both concern something that is futile (a conversation or an attempt). A hat tip to Tom Justice for hearing this one!