The "Philosophical Dialogues with my Friend Pi" are an intellectual experiment, with which the author wanted to carry out an incursion into the field of artificial intelligence, to try to elucidate what the current limits of this technology are, and find out to what extent point a machine can emulate one of the most outstanding characteristics of the human condition: the ability to reason from a philosophical point of view. Throughout these pages, therefore, the reader will find a great diversity of topics and questions that have been part of philosophical work for more than 2,500 years, many of which remain without a convincing answer. It can be said, without a doubt, that the performance of artificial intelligence for this task has been surprisingly good, which leads the author to think that artificial intelligence is being improved day by day, so that, in the very near future , there will be very few areas of human reality that will not be improved by this technology. We can only hope that this improvement will contribute to filling the gaps and difficulties that human beings have faced since they appeared on this planet.