D&D General Advice for a new DM

Your groups to big. More people makes it worse inho. Your time is finite each additional person means less face time per person.

Also increases the chances of inter PC conflict.

Big thing is the KISS principle. Keep It Simple Stupid.

Creating a whole world when you only use a small % of it is counter productive. Start small work your way up.

Work work means less focus on detail or less enjoyment after a while. You will burn out or get frustrated with the players who tend to focus on what's in front of them.
 

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...For all my obsessive planning, it went alright. I inevitably forgot to add in some plot points and scenarios and had to fudge my way through a bit, but everyone seemed to be enjoying themselves, which is all I could ask for...

Do you have handwritten notes, a plot point sheet or something you can easily refer too (one page if possible) for the next session? If you do find something helpful like this, be sure it has the elements which you find of benefit in the moment.

Related to this, it sounds like you have a lot of players. Do you have a means to keep track of different decisions PCs made (like session notes)?

...The trouble I now find myself in is mainly in regard to writing out the campaign I have in mind.
I fear I may have gotten too ambitious in homebrewing my own storyline, and now I’m kind of regretting it, and a growing dislike for my idea has begun to fester. It’s hard for me to know if an idea I have is truly bad or if I’m just too stuck in my own head...

If you don't have intentions on publishing, grab any kernel that's inspiring: character, situation, a faction or org, a module, adventure, setting, etc and find a way to use it.

e.g. Cabbage merchant from Avatar: The Last Airbender made an appearance in my campaign as a goblin who sells "cabbages." (...His business is doing too well for selling cabbages.) Everyone knew who it was right away and loved it.

If you choose to drop in a well-known module, ask if others have run it, and what their experience of that was like.

If you can provide a general outline of what your conundrum is before next session, people are pretty responsive on the forums with suggestions. Depending on the nature of above and everyone's inclinations that day, you could end up with a lot of replies!

I’m really not all too sure what advice to ask for as a baby DM, but any and all thoughts, comments, and advice are beyond welcome and appreciated.

From what you've described, it seems like you're familiar with everyone you are running the game for. You could ask them to elaborate on a particular part of their back story that complements what themes you may have in mind, then offer if they mind a tie-in to a particular NPC, faction, etc. At worse, they will not like the idea, and that is fine. They may also
glomp to the idea, and something great could come out of the collaboration.
 
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I have a few suggestions, OP, which I'll summarise as bullet points and then elaborate on. Sorry in advance if I'm duplicating any advice!
  • Don't Worry About How Things End
  • Practice The Fundamentals
  • Shamelessly Steal Ideas
  • Reward What You Want to See
  • Make Sure Your Players Are Having Fun
Don't Worry About How Things End
You generally want to set up situations for the PCs to encounter and obstacles for them to solve, but you don't want to box yourself into having a pre-determined outcome - or even to assume that the PCs will engage with all the content you might have prepared (or be prepared to prepare, as it were).

By way of example, a couple of months ago, I wrapped up a story arc (so to speak) in a game I'm running where the PCs were visiting the island that one party member comes from. They're all new to the game, so to keep them from aimless wandering, I gave them three threads they could pull at:
  1. Several people living along the island's western shore, including a cousin of the party member from the island, had recently gone missing. What had befallen them?
  2. A wealthy gnome was buying up magical constructs that people would use for farming. (The island had a lot of artificers.) For what purpose?
  3. Devil-worshipping cultists were undermining law and order in the city (on the basis, as they saw it, that it was illegitimate, being the creation of mortals as opposed to the True And Proper Order of Devils).
The party ended up more or less pursuing the first two adventure opportunities as far as they could, and while they unmasked a city councillor who was in league with the cult, they didn't unravel the cult by venturing to its secret base and destroying it. I also didn't plan for any specific manner in which they would approach solving any of those issues.

If you're running a game for a large group, you'll probably want to stick to simpler "storylines", such as exploring a mega-dungeon or some kind of episodic/West Marches-style game. In that case, you usually don't need to present plot-oriented situations: obstacles will be more physical and "already in place", such as dungeon walls, traps, collapsed tunnels, and so on. In this case you want to be open to the PCs to come up with novel ways to solve the obstacles you've put forth.

Practice the Fundamentals
I don't actually know that a lot of DMing advice suggests practicing in between sessions, but you might want to consider doing so, especially if you have weeks or months in between sessions. Consider having your boyfriend help! Try putting in, say, fifteen minutes a week on practice.

You'll very frequently be asked to adjudicate player character actions - that is, a player will tell you "I want to [Do The Thing]", and you have to decide whether they automatically just Do The Thing, whether it's impossible for them to Do The Thing, or whether it's not clear what happens - in which case they'll have to roll a die, usually an ability check. What check should they roll? What should the DC be? What happens if they succeed or fail?

You might consider offering some situation prompts to yourself or your boyfriend or someone else who's willing to practice with you, and having whomever you're working with offer up actions to take in response to those prompts. Ideally, what you want is to be able to quickly make decisions at the table on how to adjudicate the player character action. One advantage of having someone else work this with you is that you can then also ask them if they felt your adjudication was fair or reasonable.

Another thing you can try doing is thinking up an obstacle or situation that player characters might hypothetically encounter and coming up with, say, two or three approaches that they might take to solve the obstacle or situation on your own. If you're working with someone else, you can then ask them to come up with approaches themselves. The goal here is not to come up with solutions yourself and be inflexible - it's to practice thinking about solutions to obstacles and situations in play enough times that it becomes easier for you to do at the table.

Shamelessly Steal Ideas
Seriously, just do it. Either the players won't notice or they'll find it amusing. It can be off-the-cuff details you throw in for flavour or plotlines for this week's adventure. I just threw in a reference to The Littlest Hobo in the game I'm running, for instance. You could look at a show you like, especially one with a very episodic flavour or that frequently features "monsters of the week" - The X-Files, Buffy the Vampire Slayer, Supernatural, or even Star Trek or The Mandalorian could all be inspirations, among other possibilities.

Shamelessly stealing ideas also works for concepts that are more often found in other RPGs. For instance, you might check out how Daggerheart encourages players to contribute more to the in-game fiction, compared to D&D. You might not want to wholesale adopt the idea or any mechanics tied to it - and if you're new you want to avoid messing with mechanics, anyway - but if it floats your boat, you might find ways to give the other players opportunities to contribute to the fiction. I find most players enjoy that sort of thing, but not all of them.

Reward What You Want to See
Personally, I like to see the players engage with the details of the in-game fiction, so when someone brings up specific details that they call upon as part of their player-character activity, I'll often grant automatic success. For instance:
  • If you have a room containing a desk, let's say there is a key to a (trapped) treasure chest affixed with sealing-wax to the underside of the desktop, inside a drawer. Obviously, since it's completely concealed, player characters won't just notice it.
  • What I like to do is, if someone mentions searching the room, they can roll a check, and there's a reasonable chance that they'll find the key - but there's also a chance that they won't. If they make a point of mentioning searching the desk, they'll find the key automatically.
You may not want to reward that kind of detail-oriented play, but do reward the kind of gameplay you enjoy seeing as a DM. You mention upthread that the players engaged in some murderhobo-ism during the introductory July session. You can encourage positive engagement with the setting by ensuring that pro-social choices pay off for the player characters. For instance, solving the town's missing-child problem shouldn't just offer a monetary reward, it should make people in town like the player characters or look up to them, offer them discounts, suggest other adventure opportunities, spread the word about their heroism, that sort of thing.

Supposing you want to encourage, say, tactical thinking during combat. You can include environmental features that the player characters can take advantage of - somewhere to gain cover against ranged attacks, for instance, or fixtures that are good spots to shove enemies into. You can homebrew enemies with attack routines - sort of like Dark Souls bosses - that players can learn to anticipate and play around.

Make Sure Your Players Are Having Fun
One of your players is your boyfriend, right? What would you rather have? That he has fun at your games - by which I mean an enjoyable and engaging gameplay experience - or that you run your games with no consideration as to whether or not he has fun?

To be sure - if you find down the road that your gameplay preferences, or put another way the aesthetics you enjoy most in RPG gameplay - are actually very incompatible with those of your boyfriend or with other players, there's no harm in admitting that and finding other things to do together. But it's usually worth putting in the effort to give it the old college try.



Hope that all helps, and remember, as long as you're having fun, and as long as your players are having fun, then you're doing something right!
 

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