Definition of Roll the Dice
What does the term "roll the dice" mean? What is meant by "rolling the dice"?
In some casino games (the most popular of which would have to be craps), players roll the dice and then bet on the outcome of that roll.
By betting on the outcome of the roll of the dice, they are gambling.
This applies to real life as well. If you are "rolling the dice" on something, this means that you are gambling on something.
For instance - let's say that you are planning a vacation in an area that is known for its hurricanes. You hope that you happy to travel during a time that there are no hurricanes in the area.
By doing this, you are "rolling the dice" that things will be calm. You are risking money by planning this trip (as you may have to cancel if there is a hurricane forecast during the time that you are planning to stay there), as well as your health (you could be injured if you are in the area during a hurricane).
In short, to roll the dice is to take a risk on something, in exchange for some kind of a payoff.