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Free spoilers:

I booted up Wasteland for the first time in many years, and remembered basically nothing. I enter Highpool, walk around, and talk to a crying kid. It asks me to type a subject, Ultima IV style. No matter what I type, he just goes "I dunno." Things like NAME, JOB, and BYE don't work. Neither does BOY, KID, WHAT'S WRONG, CRY, or anything else I can think of.

Looking at a walkthrough, he responds to DOG, JACKIE, and CAVE.

How are you supposed to know to ask about these things? The only clue I can find for DOG is that in the shop, if you bust down the locked door, you find a pile of notes and one of them just says 'a note mentions hydrophobia.' This seems really tenuous; there ought to be some other clue. Just because some note, in a pile of notes, mentions hydrophobia, wouldn't make me deduce that this particular kid is sad because his dog has rabies. Plus, if you're playing a "good" playthrough, roleplaying as scrupulous rangers who don't break into other people's property without good reason, you shouldn't even know about that. As for JACKIE, when is Jackie even mentioned? You don't even meet Jackie until entering the cave, and asking him about the cave (which is how you learn how to get in) makes him run away.
This question / problem has been solved by 01kipperimage
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ikantspelwurdz: Free spoilers:

I booted up Wasteland for the first time in many years, and remembered basically nothing. I enter Highpool, walk around, and talk to a crying kid. It asks me to type a subject, Ultima IV style. No matter what I type, he just goes "I dunno." Things like NAME, JOB, and BYE don't work. Neither does BOY, KID, WHAT'S WRONG, CRY, or anything else I can think of.

Looking at a walkthrough, he responds to DOG, JACKIE, and CAVE.

How are you supposed to know to ask about these things? The only clue I can find for DOG is that in the shop, if you bust down the locked door, you find a pile of notes and one of them just says 'a note mentions hydrophobia.' This seems really tenuous; there ought to be some other clue. Just because some note, in a pile of notes, mentions hydrophobia, wouldn't make me deduce that this particular kid is sad because his dog has rabies. Plus, if you're playing a "good" playthrough, roleplaying as scrupulous rangers who don't break into other people's property without good reason, you shouldn't even know about that. As for JACKIE, when is Jackie even mentioned? You don't even meet Jackie until entering the cave, and asking him about the cave (which is how you learn how to get in) makes him run away.
In the building with the store, when you're inside the top part looks a little like the letter "M" (with the shop between the middle and right leg of the "M"). When you stand just below the middle leg of the "M" you should get the message:

A note tacked to the wall says:
-- cave
-- adults: raid outlaws
-- Jackie
-- Bobby's dog?
-- fix water purifier

EDIT: added screenshot
Attachments:
Post edited November 15, 2015 by 01kipper
Ah. I'm pretty sure I never saw that note before, and that answers my question completely. It does raise some others, though. Who wrote that note, and who is it meant for? What's it supposed to mean?

I get that it shows the player stuff they're supposed to investigate, but taken as an in-universe detail, it seems out of place. Is it meant to be a community task list? Points 2 and 5 are clearly tasks, and point 4 could be interpreted as a task if you know what's wrong. But I can't make any in-universe sense out of points 1 and 3. What is it about Cave and Jackie that merits writing them on a note, with no further details?
It's a list of things that are significant to the people of Highpool. They already know the details, so it's not exactly fulsome.

What is it about Jackie and the cave that warrants including them on a list? Well, Jackie is missing. And the cave requires covering up or something, considering teenagers seem to be fooling around in the cave and getting stuck down there.