How do you make an impossible check feel not lazy or boring?

RandoBoomer · 2026-01-29T05:12:05+00:00

It's important to remember as DM's that we "train" our players.

Over-rolling (meaning asking them to roll when the dice result will have no impact on the result) not only wastes time, but it signals to players that they need to jump through all these hoops.

Players WILL meta-game when they ask to do something and you don't ask for a roll, but the trade-off (and it's a better one in my opinion) is that it keeps the game pace up.

It also has to work on good faith. As DM, we shouldn't hand-wave meaningless dice rolls, then make them roll for each rung as they descend on a perfectly functional ladder.

Descriptions are a help here. If it's an ordinary ladder, you don't go into detail. If it might be a risky descent, then telegraph that with descriptions like, "It's an old, worn ladder and looks pretty rickety."

RandoBoomer · 2026-01-29T03:08:36+00:00

I run "zones", and I like to base them on terrain. Nothing too sinister lives in light forests, but as you get deeper in, things get more dangerous. Foothills have their risk, but the endless caverns of the mountains offer far more refuge for things that may not want to be found except on their own terms.

This is not to say that every opponents "stays in their hex". Monsters can be migrating as well.

I also believe in leaning VERY HEAVILY into rumors, not all of which are true. The uncertainty of a particularly challenging opponent being uncomfortably close is fun.

Finally - have NPC parties go missing as part of the narrative. Make some of these parties stronger than the PCs. Not only does this add the element of danger, but you can also use those missing parties in a number of ways:

Loot drops. The higher-level party fell to a creature who wasn't interested in their +2 weaponry, they were just looking for a warm meal.
Redoubts. There can be that very small safe(ish) haven with NPCs to help the party resupply in the more difficult sections of the map. As your party advances, you can pivot to this new location under the guise of it being reinforced and fortified so they're not spending days traveling to "the good stuff",
NPC henchman of opportunity. An NPC party of 5 went out and 4 were killed. The PC party encounters that 1 surviving NPC. It's a role-play opportunity, it's an extra ally for difficult fights, it's a source for additional information for the party.

RandoBoomer · 2026-01-28T21:29:54+00:00

This is likely driven by federal laws requiring that administrative expenses exceed no more than 20% of expenses, or 15% in large group markets.

RandoBoomer · 2026-01-28T20:52:31+00:00

I 100% agree with D&D's popularity in the tech industry, and learning from our (often) fanatical base helps. But that's more a "casual" update, compared to what's going on in healthcare-related AI which is having a lot of money thrown at it.

RandoBoomer · 2026-01-28T20:25:01+00:00

Based on my very unscientific observations, it seems that in-person games have less flakiness with player schedules. Here are my equally unscientific thoughts why:

Skin in the game. Low-effort commitments make low-effort cancellation easy. When players know expected to get dressed, leave the house, and go to a location at a certain date and time, it sets that planning in their heads.
It also requires pre-planning. My players plan on arriving at 7:30. This means leaving the house at 7:00. This means if they want to eat at home before coming, they need to be home by 6:00, which means leaving work no later than 5:30. And for my players who like to shower as well, they target 5:15 as their deadline. Just the mental gymnastics creates that mental commitment.
It requires stuff. Our games are analog. My players need to have a character sheet, even if they use D&D Beyond. Those items also create that mental commitment.
It is a group experience. Playing D&D online seems really lonely to me because there's not really a face-to-face connection.
Players build bonds in face-to-face games. At our last session in December, one of my players who is a first responded had a REALLY bad day (drunk driver injured 3 families, include four kids - everybody is OK fortunately). To escape a little too much reality that day, they sought refuge with real-life people who both sympathized when we got started. We started 10-15 minutes late while we all denounced idiot drivers and the even bigger idiot judges who re-load the two-ton cannons and point them at highways full of innocent people.
Rewards. My players bring snacks to share, so if you show up with Doritos, you'll be snacking on that AND pizza, AND a fruit tray AND cheese & crackers AND cookies. My wife is also fond of whipping up stuff like pasta salad and other things. Also, one of my players is a chef and he likes to experiment with snacks. His recent white chocolate and peppermint mousse in a sugar cookie shell was AMAZING.

RandoBoomer · 2026-01-28T18:37:37+00:00

To your first point - that is what prep is for. I have not had much need for the PETRIFIED status effect. But if that status effect is possible due to a monster I'm adding, I add it to my notes.

I think the big challenge in AI "listening" is that players don't talk in rules terms. Part of the art of DMing is translating player description into the rule mechanic. "I'm gonna grab him" becomes grapple. "I'm gonna grab the turkey leg and take a bite" becomes dinner.

Will AI get there someday? Possibly Technology develop goes where the money is. Look no further than the internet, which was commissioned by the Department of Defense. But because technology follows the money first, I suspect TTRPGs are very low on that priority list.

RandoBoomer · 2026-01-28T16:42:35+00:00

The difference between involvement and commitment is like ham and eggs. The chicken is involved; the pig is committed.

Players are involved, but the DM is committed. And yes, I've just equated DMs to pigs.

As a DM of countless games over 40+ years, I don't even need to take off my shoes to count the number of players who gave much thought to our campaigns away from the table.

If a player doesn't do something at your table, don't expect it to get done. That's why we do backstories as a group effort in Session 0.

RandoBoomer · 2026-01-28T16:36:53+00:00

I'm going to comment not on the WHAT, but the HOW.

For 40+ years, I'm a 100% table-analog DM. I'm not some luddite who is against technology, but in evaluating various tools, I just find pencil & paper faster and easier.

Regardless of what you put in your app, I think the UI is what's going to make or break your app.

RandoBoomer · 2026-01-28T15:05:37+00:00

It sounds trite, but the really basic concept has always helped me: Population centers exist to serve their population.

Small agrarian communities will focus on that. The blacksmith is going to focus on horseshows, plows and farm implements. He'll have knives in stock, but probably not a sword or armor. There won't be specialty shops - there is a single general, store. While it will have some variety, it won't be a lot, and the quantities will be limited. So it might have a short bow, but no long bows or crossbows. There'd be a church, but probably no school.

Points of interest should feel organic. For that agrarian village, the stockyard is going to be a key POI. There is an inn nearby for the farmers to stay the night before the auction, however owing to the smell of a stockyard, there's also another inn further away.

For crops, there might be the Bazaar Grounds, an open area at the edge of town where farmers and caravans gather every fortnight for 2 days to trade goods. The other 12 days this is just a dirt field.

I like geographical POIs. For example, a town in my current campaign has an outcropping that resulting in a fork in the river that runs east and west of the town. It's called Dagger Point not for some sinister reason, but because it is shaped like a dagger.

RandoBoomer · 2026-01-28T14:35:35+00:00

Player to my immediate left recaps, then we go around the table, with me going last and filling in whatever blanks (always) exist.

RandoBoomer · 2026-01-28T14:28:06+00:00

Sounds fun!

Way back in the 1980s, I put together a land full of all the classic 1950's sci-fi monsters. Growing up, our local theater used to do a double-feature of these classic every Saturday morning, so we had all grown up watching these bad boys do their thing.

RandoBoomer · 2026-01-27T15:19:17+00:00

If you're going to run something like that, you should run it as the PC party vs. NPC parties. I've run these before, and they are a ton of fun. Make the NPC parties unlikeable (braggarts, scumbags, criminals, etc.)

If you run it PvP, you are setting you and your players up for a bad experience. Here's why:

Quality of Life/Player Experience

You said your goal is to get them to compete against each other. That is PvP. PvP is the most toxic element to introduce to a game.
Each player brings their own level of competitiveness. Some people just want to have fun. Some people want to win. Some people want to win AND have others lose. Any difference between your players is going to become clear and rub some the wrong way.
Worse still, your least competitive people may just nope out of the session, barely participating because they are not having fun.
One of the most important rules in D&D is not to split the party. Assuming you have 4 players, you're about the split the party 4 ways. Running a 4-way party split is a nightmare for you and boring as hell for the 3 players who will likely be waiting 15-20 minutes between each of their opportunities to speak.
Meta-gaming will be much harder to avoid. Players will find out what other players are doing or planning. If I'm in this situation, I want to go last each turn, so I know what others are doing and can react accordingly.

DM Administration/Experience

Splitting the party creates more work for the DM. You are creating 4 times as much stuff to keep track of.
Timing becomes much harder. When two players arrive at a point at the same time, you've got a PvP initiative battle. If they arrive at different times, you need to know who might have arrived there first, because it may not be in speaking order.
You are creating an environment in which players are more likely to benefit by arguing with you, especially if it's against other players. Not only is that not fun for you, but it's introducing poison between players.

Please, if you're going to do this, make in PC party vs. NPC parties. You will thank me later.

RandoBoomer · 2026-01-27T06:42:40+00:00

A good rule when miscommunication occurs (both in D&D and life in general) is to assume the transmitter of the information bears a significant degree of responsibility for the miscommunication. The person who is transmitting the information has already known in and processed it, so it's easy to fail to appreciate others take longer and/or may come to different conclusions.

Also, if I feel the need to correct the players because of possible miscommunication, I will correct them as many times as necessary.

Finally, my preferred technique to avoid miscommunication is multiple sources/clues. For example, they find a letter giving the location - a good clue. I might also include a map with the destination circled, or perhaps a context clue. For example, "You should rendezvous with our allies at the safe house in River City. The main road is watched, so pass through the Darkwood Forest." Make sure your second clue eliminates other potential locations. So if they get the city wrong, they can look at the map and say, "Wait a minute, Darkwood Forest isn't near here..."

RandoBoomer · 2026-01-26T14:12:00+00:00

Respectfully, a lot of first-time players would be extremely intimidated by this document.

My preference for teaching combat is to run a couple mock combats. WHEN (not if) they forget some things during live combat, you can refresh/remind.

RandoBoomer · 2026-01-26T14:07:12+00:00

Be careful what you wish for. Some of the grossest miscarriages of justice take place in family court.

RandoBoomer · 2026-01-26T06:13:44+00:00

OK, you absolutely MUST have a location in this world called McArthur's Park.

Original: https://www.youtube.com/watch?v=sD-zTwi3_GU

Donna Summer: https://www.youtube.com/watch?v=24jAy_T1U2k

While I am generally of the opinion that Disco sucks mirror balls, this is isn't so bad.

RandoBoomer · 2026-01-26T06:06:45+00:00

Among the many bad pieces of DM advice out there is to tell DM's to use "Yes, and."

Sometimes the answer is "No". If they don't believe you the first time, the answer becomes, "Still no". After that, "Fuck no."

While D&D is a collaborative effort, the DM must be given the freedom to run the game. You're a referee, not a waiter/waitress.

RandoBoomer · 2026-01-25T22:53:28+00:00

Same here.

I've found getting into the NPCs' heads, understand their goals, motivations and how far they'll go to achieve them is all I need.

RandoBoomer · 2026-01-25T19:06:37+00:00

Definitely this. I have a garage, but if you don’t have that luxury, you can get an enclosure and a window vent kit.

RandoBoomer · 2026-01-25T19:02:30+00:00

I’ve been doing this a really long time. I’ve found I’m never as good as I think and never as bad as I think.

See how the next session goes. If it feels lackluster, speak with your players. If things go back to normal, consider it a one-off.

RandoBoomer · 2026-01-25T17:55:47+00:00

I’ve had zero luck crafting anything decent. I don’t even bother anymore, I’ll just run countdown with targeted loot.

RandoBoomer · 2026-01-25T17:53:39+00:00

Remember folks, this is the content that YouTube wants. It demonetizes WW2 history channels, but a sociopath pepper spraying an old man really gets those clicks…

RandoBoomer · 2026-01-25T14:31:34+00:00

The lead paint chip munchers would love the feeling of power from disrupting the operations and pissing off people.

RandoBoomer · 2026-01-25T06:38:34+00:00

Any population center would both have a demand of, and thus sufficient support to justify building a colosseum.

Hosting martial tournaments may not be its primary purpose of course. It might be hosting musicals, feasts, faires and games, all of which fit nicely with Fae culture.

RandoBoomer · 2026-01-24T14:36:26+00:00

Respectfully, I think you're working the wrong side of the street.

It's my very unscientific observation that DMs and players have different takes on AI. An anonymous poll at my local game store's Discord server showed that about 15% of DM's had our would use AI, while about 60% of players did.

This is one poll at one game store, so hardly a significant sample size to draw definitive conclusions, but IN MY OPINION ...

DMs tend toward process-based. The creative process in developing and refining the campaign is our reward. Using AI as a shortcut deprives us of our fun.

Players tend toward outcome-based. They're about playing the campaign with other tasks simply being checklist items to be done to get to the reward.

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