I like this word because it does have a few meanings and it is also one of my favorite foods. It's also a somewhat silly word.
Pickle: a cucumber that has been preserved in brine, vinegar, or the like.
Pickle: A liquid usually prepared with salt or vinegar for preserving or flavoring fish, meat, vegetables, etc.; brine or marinade.
Pickle: a troublesome or awkward situation; predicament: I was in a pickle after the check bounced.
Pickle: A sour, disagreeable person.
Pickle: a situation in the game of baseball that occurs when the baserunner is stranded between two bases and is in jeopardy. When the base runner attempts to advance to the next base, he is cut off by the defensive player who has a live ball and attempts to return to his previous base before being tagged out. As he is doing this, the defenseman throws the ball past the base runner to the previous base, forcing him to reverse directions again. This is repeated until the runner is put out or reaches a base safely.