Plato's Five Dialogues is comprised of five short dialogues, each about 20-40 pages, and which all star Plato's teacher Socrates as the main speaker. The dialogues have to do with the trial and execution of Socrates by the city of Athens in 399 BC on the spurious charges of corrupting the youth of the city.
A person I know saw me reading this book one day said something like, "Plato? You read that for fun?" I think he had the idea that Plato is a hard read or a slog to get through, but nothing could be further from the truth. The dialogues are short and easy to read, and Socrates and the people he banters with are witty and clever. Socrates at times comes off as even a bit of a smart-ass. I think a thoughtful high-schooler would not find this book intellectually out of reach.
The first dialogue is called Euthyphro, and is a dialogue between Socrates and his friend Euthyphro outside the court building in Athens, where Socrates is about to be charged. Yet, Socrates is not interested in talking about that, he wants to know why Euthyphro is there. Euthyphro explains he is suing his father, who killed a slave who had himself killed a man. Euthyphro's relatives think he's crazy to sue his own father, but Euthyphro thinks it is the pious thing to do. Socrates digs a little deeper, hoping Euthyphro can explain to him what piety is, since he's so sure of himself as to sue his father in its name. Euthyphro cannot explain it adequately, even with Socrates's prodding, and the dialogue ends inconclusively with Socrates due at his trial.
The second dialogue is the famous Apology, when Socrates defends himself before the 500 assembled men of Athens on the charges that he has corrupted the city's youth. There is some debate among scholars about how much of Plato's works are truly the words of Socrates, and how much are Plato's own ideas that he put in Socrates's mouth. But there is little doubt here that this is a very close account of Socrates's actual speech in his defense, as Plato claims to have been there and this was apparently written soon after the trial took place. Despite a moving and powerful speech in defense of the philosopher's life, and that he had done nothing but help the youth of Athens seek wisdom, he is found guilty and sentenced to death.
The third dialogue is Crito, and is between Socrates and his old friend Crito, who has bribed the jailer and found a place for Socrates to live in Thebes, if he'll flee with him. Socrates however refuses to leave his cell, and walks Crito through a neat little philosophical argument, at the end of which Crito sees that Socrates could not possibly escape if he really meant all the fine words he said at the trial, for he had said that even if found guilty he would face death bravely because he knew he had always pursued the truth.
The fourth dialogue, Meno, seems to be something as an outlier since it takes place some unspecified time before the trial, when Socrates is speaking with Meno, a young man from a wealthy family in Thessaly who is visiting Athens. But it turns out to be necessary to understand the final dialogue, for here Socrates convinces Meno that the soul is eternal and people do not really learn, but only recall things that the soul already knew. He quite cleverly walks one of Meno's slaves through a geometry problem, with only an occasional suggestion helping the slave to find the right answer, as a demonstration of his theory.
The final dialogue is Phaedo, when Phaedo, who was at Socrates's side on this last day in prison before his execution, recounts the events of that day to a group of philosophically-minded men. That is something of a framing story, as the bulk of the dialogue is taken up with Socrates's own words describing his view to his friends that the soul is immortal, and that one who has lived an ethical, philosophical life may look forward to an afterlife in the company of the greatest of heroes and thinkers who have passed on before, In typical Socratic fashion he convinces them with beautiful arguments, calmly and rationally addressing all their objections, and ends with a moving description of his view of the world beyond. At the very end, he takes the poisoned chalice offered by the executioner with utmost serenity and drinks it without complaint, even chiding his companions for weeping when he himself is happy to see what comes after death.