Risky proposition is a term used to describe a situation that involves taking a chance or a risk. It is often used in business and financial contexts, where a risky proposition may involve investing in a venture with uncertain outcomes. The term can also be used to describe a situation in which someone is asked to do something that could have negative consequences. The crossword solution for this term is 'DARE', which is an acronym for 'Dangerous Adventure Risky Enterprise'.