The Long Goodbye: Hello, Questions!

Okay, does somebody maybe want to explain to me the huge disconnect between Picard’s voice over regarding the holo-deck and his acting as though he’s never been in a holo-deck before? How about the fact that holo-decks are often used for training by all sorts and ranks within Starfleet and yet the captain of a ship in the fleet has never been in one before? What the hell?

Was this maybe the first ever episode written involving holo-decks? Also, how does a holo-woman leave lipstick on your face even after you leave the holo-deck if everything you experience in the holo-deck is actually nonexistent? And how did Picard not realize he was asking Dr. Crusher on a date and had made the party too much of a crowd?

Also, how come there’s holo-deck technology to trick the crap out of your sensory perceptions but there’s no purely phonetic guide to the strange alien greeting which if mispronounced in the slightest leads to catastrophe? And why isn’t the proper phonetics of said speech not loaded into the the computer library where it can be accessed through the holo-decks so Picard can learn every little inflection possible to make his performance of the greeting impeccable?

And how is it possible that perfectly quaffed Dr. Crusher doesn’t know how to powder her nose and is forced to take her cues from a flour-flushing floozy?

And why the hell would would-be-humanitarian-of-the-century Captain Picard not tell a fictitious character in the middle of a profound existential crisis that his wife and children are real and waiting for him to come home even if it’s only to prove your humanity through the mask of fiction?

Is Picard really not so great a man as everyone likes to make him out to be?