DMing my first adventure tomorrow, what was your first session like?

I’m finally taking the plunge and DMing a 5e game with some friends where they’ll all be thieves (inspired in part by the Marielda arc of Friends at the Table and the Sly Cooper series). I’ve read a bunch of the standard articles that are filled with first time DM tips, so now I’m wondering if any of you have fun (and/or horror) stories about the first time you ran an adventure.

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One thing that’s really good advice that first-time DMs often miss is that you should devote a large portion of your first session (maybe the whole thing) to collaboratively working with your players on character creation.

This doesn’t mean necessarily making sure that the party is balanced between classes (that’s pretty easy to fix later if it’s an issue), but making sure that there are good hooks in each character’s backstory to give them motivation for the adventure you’re setting out on and their relationships with each other and highlighting if there are going to be problem areas of friction between the characters if the players role play them well.

For first time players, it’s good if they all are “good” alignment characters (even if they’re all theives). You can have very fun times with characters that clash ideologically with a party mixed between good and neutral or good and evil, but that requires a very steady hand from the DM and a set of players who are good at recognizing the line between “interesting story friction” and “disruptive to the flow of the game and everyone’s enjoyment.” It’s maybe not something I would want to take on for your first game.

If you think that “all good” characters won’t work for your game, make sure that there is a reason or loyalty between the characters so that they’re basically on the (sameish) page. Again, this isn’t a hard and fast rule, but not following it can cause a lot of personal tension in games that’s tough to deal with for a first-time DM and first-time players.

The one reason I emphasize doing this as your first session, is that it’s much, much easier to clear up these issues in character creation and in group creation than it is later on. Yet most first-time DMs skip through this or really want to get going on the first session because there’s a (real) fear that if you don’t kick off the first session with an adventure that has some momentum to it there is much less chance there will be a second or third session. But believe me, that early character work saves so many headaches later on.

Also: schedule! Set a regular expectation that you will have a game every week or every second week. Make sure the next session is on the books before everyone breaks for your current one. If you are going to have sessions less than every two weeks, make sure there are out of game things you can do to keep your players thinking about the game while they’re gone.


My first time DMing was for a few buddies. I basically had to force them to leave the bar where they started and they ended up trying to burn down the forest.
We were all new so we had a lot of fun and I learned a ton just by finally doing it.

For the first game I ever DM, I made the mistake of not establishing why the characters were all in a party and on the same page, as Dkaszor put it. This meant that I had to do a little railroading to give the characters an in-universe reason to be together, which wasted a bit of time that could’ve been spent on something more interesting, IMO.

Like @dkaszor notes, make sure to spend your first session, as well as a good chunk of time before or immediately after that session, focused on character (and world) building. Focus on the specific in-fiction character types the players are developing, but also on the meta-level priorities of the players themselves. Presumably you’ve already done some of this legwork in bringing together a group of people to begin with, but you want to establish early on exactly what kind of game your players expect. Some like tactical combat and dungeon crawls, some like rules-based numeracy and character-sheet MinMaxing, while some prefer to focus on in-character roleplay and narrative development. While it’s certainly possible (and fun!) to focus on multiple priorities, if this is going to be the case, you want your players to know this in advance. It can be very difficult to keep everyone interested if your combat-focused Fighter is getting bored every time the party needs to sheathe their weapons and go talk to a diplomat to gather information.

As far as character building goes, whenever I start a new game (or introduce a new player) I like to give my players a list of questions to help them think about their character. D&D 5E already does a pretty good job of this on its own, but I try to supplement the Background elements with the following questions:

  • Name one thing your character aspires toward. What is their primary motivation or goal?
  • Name one thing your character is afraid of.
  • Name one thing your character would never do. Something outside of their personal “code”
  • Does your character have family or close friends? Who are they, and what kind of relationship do they have with your character?
  • How has your character’s upbringing influenced their worldview?
  • Name one thing your character would kill for. This goes beyond typical mercenary work — something (or someone) so important that they could justify taking someone else’s life over, without question.
  • What one possession does your character value most?

The tips above are all good and should go a long way. I would add that a really good thing to do is to have a list of random names prepared in case you have to come up with an NPC on the spot. Since you’re playing D&D you could just write down some of the names suggested in the book, and then cross them off as you use them.

My first time DMing was the starter adventure for 4e. No one in our group had played before, and it took a while before we realized the amount of freedom we had. In particular, there was an encounter where to players, big strong Paladin and an agile Thief, were facing off against a couple of Kobolds on the other side of a pit. Instead of running around the pit, the Paladin said “I’ll boost the Thief so he can jump across the pit and stab the hell out of those dudes”, so I had him do a strength roll and the Thief did an attack. Both of them critted and it was a pretty cool moment.

Then there was the first adventure I made myself which involved the players fighting a dragon in a sewer. The Wizard thought (correctly) that it would be pretty cool if he could surf the sewage while blasting spells at the dragon.

These days I’ve grown pretty tired of combat heavy D&D-style RPGs, but I still value the good times I’ve had with them.

For what it’s worth, 5E is much better at non-combat stuff than 4E (mostly by liberally stealing ideas from Dungeon World)

It is definitely better, but I still hate that the GM has to keep track a bunch of numbers and roll dice constantly. Combat just feels like a slow slog that is more about saying numbers at each other than an opportunity for story to happen. But this is just my GM side talking. I actually think 5e is pretty fun to play if you don’t have to worry about all that stuff.

it was a star wars saga premade and it expected players to help somebody getting chased by storm troopers and my players just didn’t and she got arrested and the rest of the adventure then had to get improvised. So from then on, I always just think more in terms of what NPCs and groups of NPCs want and what they work towards rather than making anything dependent on the players helping anyone.

Ah, see I’ve always played using Roll20, which tracks a great deal of the numbers and math for you.

A friend of mine made his own homebrew system sometime in middle school. I then made my own version of the same basic game and started running that for about 2 years. Neither of us had played DnD or any other PnP RPG beforehand, since apparently tabletop nerds will spontaneously create game systems if their environment will not supply them with one. They will then incessantly argue over which is better. I don’t remember a ton of details, since it was 15 years ago, but it relied heavily on 2d6 rolls. Another of my friends did a lot of the character/monster art and we had an oversized white binder full of our work.

The first session consisted of my friends just trying to sabotage every single rule I had come up with and me over-relying on the most stereotypical OCs possible. At one point in the session, I had a blind moleman/myconid swordsman show up and my friends made fun of him so relentlessly that I had him get eaten by a sandworm. It was a beautiful trainwreck and I regret none of it.

Once we got to high school, a new kid introduced us to DnD and I abandoned my old system.