@savagemonk,
Well the answer which I will provide is more than likely not what you are looking for but it is my experience.
Philosophy, as a whole, is a joke. A very very long joke with a somewhat fuzzy punch line. It is true that nothing is ever resolved and it is true that we just keep spinning our gears trying to find answers to questions which have no real answers.
But what philosophy IS good for is the process. Critical thought is one of the most important things in the world next to passion. When you combine the two, you can accomplish almost anything. Philosophy is a practice. It was never truly intended to unlock all of the secrets of the universe. The universe is too massive for one subject to encompass it all. No, instead, philosophy was intended to be a jump point of sorts. A place to start. A place to expand until you had the necessary knowledge, wisdom, and understanding to find the answers on your own.
If you want to talk to him about philosophy then don't waste your time. If you want to talk to him about the importance of passion, critical thought, and living life to the extent of understanding the world around you in the best way you possibly can, well just say that then.