As an avid player of video game RPGs, I was always aware of Dungeons and Dragons, but my direct contact with the system itself was limited. When I was about 10 or 11 years old I convinced my dad to buy me the boxed set of "Red Steel" which was sold by TSR at the time, but I couldn't understand any of it. It came with a lot of campaign materials like a map, description booklet and even a music CD, but the rules were entirely missing and I had no idea how to make a game out of it. So despite the cool box art, it was quickly shelved and forgotten.
In the early 2000's I played a lot of games explicitly based on the D&D system or a derivative. Neverwinter Nights, Baldur's Gate: Dark Alliance, Knights of the Old Republic, and even action RPGs such as Diablo 2 and Champions of Norrath used systems very similar to the stat-heavy pen and paper. I quickly grew tired of this system as I perceived it to be deeply imbalanced. Gamers by nature seek to optimize or exploit whatever game system they're given, due to every software being exploitable by nature and the drive in games to win at all costs. Specifically I found most magic spells to be way more useful than non-magical attacks, even if they were nerfed in damage they always had more utility, and any Dexterity based build was always better than a Strength based build, especially if Dexterity measured chance to hit, which made Strength utterly worthless.
Suffice to say, this didn't endear me to seek out the pen and paper game, which at that time was transitioning from 2nd edition Advanced D&D to 3rd edition, and had gained a reputation as something quite complicated, cumbersome, and requiring a large monetary investment to get the full experience.
During my senior year of high school I was invited by a friend to start a D&D group. We the players bought the 3rd edition Player's Handbook and he bought the Dungeon Master's Guide, and another player bought a Monster Manual. We met at his house and played about 4 sessions. I enjoyed it but I had played enough games by then to know how to optimize my char, so like every highschooler who played 3rd ed I played a Rogue dual wielder assassin with throwing knives.
I only really got into Dungeons and Dragons in 2012, when my youngest sisters were in high school and would spend every day of the summer at home, bored, or on their Nintendo DS. I figured board games at least would be a healthier form of entertainment, so after a few abortive attempts at playing Monopoly and RISK, I went and bought the "Starter Set" for D&D Essentials.
Little did I know at the time that the Essentials line was slowly dying and a new edition of D&D was on its way, but the opening campaign of the Starter Set was a unique gaming experience to my family and enjoyable to everyone, so I went all in and invested in the core Heroes books, the Rules Compendium, and the two boxed sets of the Dungeon Master's Kit and Monster Vault. My sisters generally despise being involved with my games but they kept returning for the Dungeons and Dragons sessions, even if our playtimes were sporadic and few and far between.
We played through the Starter Set adventure, and next through Reavers of Harkenwold, the adventure that came with the Dungeon Master's Kit, and Cairn of the Winter King, which came with the Monster Vault. Somewhere around the middle of Cairn of the Winter King we all just drifted off. As a DM I didn't really know what I was doing and making a lot of it up on the fly, and that caused issues when my judgement was wrong, and was only exacerbated by issues inherent in D&D 4E.
A common complaint was that play simply took too long: It took an hour to get set up - to get out character sheets, tokens, to set out the maps and place monsters. In every case I didn't even read the module before starting so we'd waste time where everyone simply waited for me to read the next step of the adventure and nobody really knew the rules so gameplay was halted at many points where players and the I just read the rule books. And finally combat in 4E just inherently took too long - it was much too based around modifiers and gridded 'tactical' play where a lot of time would be spent just calculating damage, to-hit probabilities, and bonus modifiers and detailing powers. I personally did not enjoy running combat and I didn't like the expectation that every game session had to revolve around, or at least involve an instance, of combat. Cairn of the Winter King was a straight dungeon crawling adventure and was almost purely combat based, and I think that focus, along with external life interruptions, caused us to lazily abandon D&D play.
A few years later while perusing the local bookstore mega chain, I noticed that there was a whole new collection of D&D books and one in particular looked very appealing to me: The Hoard of the Dragon Queen adventure module, which had a White Dragon breathing ice across the cover. My youngest sister enjoys dragons so I figured she'd be interested, and I thought it would be a good idea to get back into pen-and-paper gaming. Now, at the time I had no idea that there was a 5th Edition of Dungeons and Dragons and that the adventure module was built for that. There was no edition version listed on the covers and the branding simply said "Dungeons and Dragons", which is exactly what the Essentials books said on them, so I assumed they were the same thing. For comparison, 1e, 2e, and 3e all prominently displayed "Advanced Dungeons & Dragons", "Advanced Dungeons and Dragons 2nd Edition", or "3" and "3.5" respectively on their covers and in their brand, so it was easy to avoid confusion. It's only after we played the first few games that I noticed something was amiss.
My family's PCs were just WAY TOO powerful for Hoard of the Dragon Queen. There's an encounter in the 2nd chapter where the PCs face off against a powerful villain named Langdedrosa Cyanwrath, a half blue dragon fighter who's supposed to challenge one of them to a duel, humiliate them, and walk off. This was supposed to 'raise the stakes' in story and give the PCs a hook for vengeance. My players beat him to the ground, stripped his clothes and took his lunch money. The next few chapters are fights with bandits and a dungeon crawl meant to be somewhat challenging, and my players rampaged through the whole thing, with my youngest sister threatening all the NPCs with an "intimidating glare" and trying to force them to surrender, and basically walked out danger and consequence free. This caused me to actually research the system to figure out what was wrong, and where I came to the revelation that my players had brought over relative superheroes from the 4th Edition of D&D into the more average power 5th Edition world.
I figured I'd need to do some serious research into making this edition conflict work, and to make the game more enjoyable for my players and for myself as well. For one, I'd have to actually read the Essentials' Rules Compendium and Dungeon Master's Book, which I think I read once before maybe but they had contained so much repeated copy and paste information from each other and the Player's Handbook that I had originally just skimmed over them. And I went out and bought the new (5th edition) Dungeon Master's Guide, which I thought would be the core rulebook of the game as that's what my highschool friend had presented it to me as.
Well, I was initially disappointed as the Dungeon Master's Guide (5th edition) contained many options and descriptions for creating a world, characters, and adventures, all of which I could do on my own without needing a guide, or just take from a prepublished adventure module which would render the DMG obsolete. However that was only on a first pass and after subsequent play sessions and more testing I found the DMG to be very useful, however that didn't solve my immediate problem.
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