We're just hanging out, man

Question

_{This puzzle is part of the Monthly Topic Challenge #3: Pencil and Paper Games}

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I'm a bit unsure who to ask about this...

You see, there's this guy I know. I say 'know' - we're not close mates, come from entirely different walks of life really. It's more that - for some reason I still don't fully understand - he seems to trust me, value my opinion... Because over the last ten years, he's contacted me several times when he's been going through some kind of personal difficulties - crisis of faith, relationship problems... that kind of thing. Except he doesn't tell me exactly what the problem is. No, it seems this guy has decided that the way to help him cope with his troubles is to play a game...

So each time, he gets in touch, we exchange correspondence, have a bit of back-and-forth, he invites me over after work, then we both drink rather too much and have a game of hangman - you know, the paper-and-pencil game? He chooses a secret word and I have to guess the letters from it. And I know everyone has their own slightly different way of drawing the gallows, etc., but in this guy's rules you effectively got ten chances to be wrong, and on the eleventh that was it - game over*. Sometimes he won, sometimes I won, and no matter what the outcome he'd thank me for helping him clear his head, said I'd "made his mind up for him", and then at the end of the night he'd send me on my way with a little something for my trouble, and I'd try to stagger home but always wake up in a ditch the next morning with a terrible hangover, very little recollection of the night before, and covered in goodness-knows-what. Happy days...

Well, the other day I received an initial message from him inviting me over for another game, but the strange thing is: since then I haven't heard a peep out of him. He's gone all cold, like - isn't answering my replies asking him when we should be meeting. I'm worried something might have happened to him.

For some reason I've kept all the old games of hangman we've played. I'm wondering if there might be some clues here to help me work out what's happened this time. Only thing is, because he likes his secrecy we always play in a code. Probably should have mentioned that sooner... Each letter of the alphabet is represented by a different symbol. Always the same code each time. Unfortunately, I don't have the key to hand. And I can't actually remember what the solutions were - like I say, we always drink A LOT while playing - only that I'm sure there was some kind of theme to them. I just wish I could recall what it was...

Can you help me? It might help you to know that I always play a particular strategy to my first guesses - one that a lot of players of the game use. And then I have another strategy for the next few guesses that I often resort to using... After that, it's just sensible guesswork.

I really hope he's okay.

TASK: Describe the narrator's hangman-solving strategy, deduce the five solutions to the previous games, and thus the identity of the 'guy' who instigates the games. What's happened this time?

^{* Note from OP: This is the rule-set I always played when I was a kid: Five lines for the gallows (including the little strut to support the top-beam), then head, body, two legs, two arms. I know other people might use more or fewer lines in their construction, or do the arms before the legs, even sometimes adding feet or facial features if they want to give more chances (or extra struts at the bottom of the gallows if they value decent carpentry techniques and structures built to last...). In any case, I've stuck with what I know :)}

Answer 1

I believe your partner is

King Henry VIII of England,

the words are

his wives' surnames (or equivalents thereof),

and the significance of your games is that

hanging signifies that he will have the wife in question executed rather than merely divorcing her or waiting for her to die.

The five words so far are

ARAGON, BOLEYN, SEYMOUR, CLEVES, HOWARD.

The sixth must have been

PARR

and the reason you have not heard from him is that

Catherine Parr outlived him

and therefore

your pastime with good company has come to an end.

Your initial strategy is to

guess the vowels in alphabetical order

but I'm afraid it isn't clear to me what your not-always-used second stage is, though it seems that your next guesses are quite often

S, R, N in that order. (I might have expected TNSHR, or something similar, on letter-frequency grounds, but for any variation on that theme your first guess after the vowels should be T and it clearly isn't.)

The words, along with your incorrect guesses, are:

ARAGON  EIU BSV
BOLEYN  AIU SR[MWGCD
SEYMOUR AI N[B
CLEVES  AIOU RN[GB
HOWARD  AEIU N[BMLC

where

we can see the initial vowel guesses and then the other things you've tried. I don't know what letter [ represents, though an obvious guess would be T.

He has indeed had

a "crisis of faith" (it was under him that the Church of England seceded from the Roman Catholic Church) and "relationship difficulties" (he had six wives and killed two of them).

In comments, JLee asks how I figured out which letter was which.

I was expecting the first step to be either "common letters, in order according to some widespread estimate of letter frequency" or "vowels, in alphabetical order". I looked to see what symbols consistently appeared in what order in the wrong guesses, and aside from not knowing what order > and * come in this was sufficient to determine the order of the first few symbols, and conveniently & comes out as probably O with either version of the first step. So then, looking at the first game, I asked Qat for words A-A-O-, E-E-O-, or T-T-O-, looking for things that might be one of a set. There weren't many plausible candidates (some very obscure words along with AMAZON, ANALOG, ARAGON, AVALON, and TATTOO), and after a moment it occurred to me that ARAGON is obviously one of a set, and after another moment that lots of other things in the question would make sense if that were the right first word. Then I checked that all the other games were consistent with my theory, and the names in those games gave me most of the other letters used in the games, the only exception being [.