Ever since I started meditating upon "The Fool" I keep thinking of the ending line of a song that Danny Kaye sings in The Court Jester. "I made a fool of myself." That 1955 movie concerned a man who played a jester in order to gain access to the royal court and assist in a plan to place the rightful king on the throne.
Although almost every tarot deck depicts the fool card as an innocent lad, or perhaps a seedling or a newly hatched creature, in reality fools are not so simple. The vocation of jester was a complex one. Jesters came from all walks of life. Unlike the upperclass or the skilled craftsmen, you did not have to be born into a jester's family in order to become one.
Jester's usually started out small. Much like the sidewalk entertainers we see in tourist towns today, the jester would mark off his stage and perform as people gathered. At the end of the show he would pass his hat for donations. The shows ranged from simple mime acts to acrobatic feats, tightrope walking, singing and dancing, to magic. As the jesters abilities grew, his performance became more polished. If he was one of the lucky few, he would be asked to audition for a position at court.
Once at court many jesters were sought after by their employers for more than entertainment. After the costumes were off and the castle was to bed, the jester could be called upon for conversation, advice or perhaps just a listening ear.
In this aspect the jester was far from being the innocent youngster that most sources on tarot like to say he is.
Another aspect of the fool is someone who is "playing the fool" as a deception. This would be a man who pretends to be inept while grocery shopping in order to get the women shopping nearby to feel sorrow for him and want to help him out. This would be the pool hustler who pretends they can't play the game and then takes your money in a few easy shots. This is also the woman who pretends to be helpless and lets someone else change the tire on her car.
The point that I have reached is that when the fool card is drawn, it cannot be taken at face value. It may well be a warning of deception. Either your own, albeit unknowingly, or someone you will meet.