5 min read

Welcome to Waterdeep

Our story begins as a group of adventurers meet for a drink at the Yawning Portal, a historic tavern at the heart of the Castle Ward in the city of Waterdeep. What starts as a normal, albeit rowdy night, quickly takes a dark turn.
Waterdeep: Dragon Heist

You can find my prep notes for free on Patreon.

The What and Why

In life, there are moments when you realize you are in over your head. Running your first adventure is one of those moments. As a player, I was always thinking that I’d enjoy being a DM. As a person, when I find something that I get excited about, I jump all in. The phrase “If you’re gonna get wet, you might as well go swimming” comes to mind. Except that I go to the high dive and cannonball into the deep end.

I’ve been on a lot of subreddits where people are posting that they are new and are looking for advice. Most of the comments are about relaxing, reading the adventure, and having fun. And those are all important. I wanted to provide something more detailed that could serve as a concrete example for someone starting out.

This is why I'm chronicling my adventure. All the awesome moments, epic fails, and the work that goes into the background. I plan on splitting my posts into at least two types. The first is Recaps and Retrospectives. I will be recapping the session, talking about how I felt about certain scenarios, and trying to identify what went well and what didn’t. The second type will be Session Prep where I plan on sharing my actual game time notes in all their brutal glory.

My hope is that this helps someone somewhere. Whether it be feeling more confident for their session or generating some ideas.

So without further ado, on to Waterdeep.

Getting Ready For The Game

I chose to run the Waterdeep: Dragon Heist campaign for two reasons:

  1. I love Jarlaxle as a character
  2. It was so different from the other two adventures we had already done.(Lost Mines of Phandelver and Rick and Morty)

I watched a lot of YouTube videos and read a lot of articles trying to get ready for my campaign. In the end, I leaned into Sly Flourish’s Lazy DM approach. It was the first time that I had found a structure that I felt was battle-tested enough for someone new to try out. It also is a great framework for thinking about your campaign as a whole.

If you aren’t familiar with Sly, he is the one responsible for the Lazy Dungeon Master and Return of the Lazy Dungeon Master books. I highly recommend them as they are great at giving a starting framework to your planning.

However, for a first-time DM like me, they turned out to be a bit too loose as guide rails, so my notes ended up being more detailed. I think an experienced DM can do wonders with barebones notes (see Matt Mercer’s Gametime Notes. WARNING! Spoilers for Critical Role). But this being my first time, I needed more details and outlines available as we went.

The one thing I can’t recommend enough is what Sly did in his video in preparation for his own Dragon Heist campaign.

The way he laid it out came in four parts.

  1. The pre-session email
  2. Setting the context
  3. Creating the characters
  4. Running a short session

The Email

The email aims to set expectations for Session 0. This was the first time my group had ever had one and this helped crystalize its format. IIn the email, I outlined the session's flow.

  • Review the contents of the email
  • Adventure expectation
  • Provide additional context as to what was happening prior to the start of the adventure
  • Important facts that they needed to know about the world they were entering
  • Creating character backstories
  • A quick session during the back half of our time
  • My expectations of them coming into the session

Here is a link to a Google Doc with my email. Feel free to use it.

Session 0: Welcome to Waterdeep

The campaign context and important facts can be found in my gametime notes. I did expand a little based on any questions they had but we spent the bulk of the session on the characters.

This actually turned out to be a lot of fun. We started by having everyone go around and share what they had come up with so far. I then started spitballing backstory ideas that could link them all together. What started as me throwing out ideas turned into the entire party getting excited once a few landed. Keep in mind, while I threw out many ideas that didn't stick, it got everyone thinking.

After fleshing out the characters, we ran the first three encounters of the campaign. And it was at this point I realized I was in over my head. I was a bit caught off guard by all the things a DM has to keep track of. Because of this, I missed some good opportunities.

In my version of the campaign, instead of a Troll, I had a Merregon come out of the portal (same as the Lazy DM). Unfortunately, I hadn’t spent any time thinking about how to build tension and introduce the devil. Much less the actual mechanics of the fight. So I stumbled a bit.

First I had Taman, the human rogue of the party, notice a sound coming from the Portal due to his passive perception. No one else could hear it for a few moments and then the character with the next highest passive perception could hear it as well. Viigo, the dwarf cleric, got up and went over to look into the Portal. This is when I had the Stirges fly out of the portal, soon followed by a gauntleted hand that gripped its side. As it crawled out, I took time to detail how the dwarf found himself staring at a bronze faceplate bolted onto the head of a demon.

And then… I realized that this thing could do some very real damage to the party. And then I panicked. Instead of the creature doing something dramatic, like swiping at a table next to the party, it spent a turn “getting its bearings having found itself in a rowdy tavern.” Compared to all the alternatives… I find that a weak play. But I didn’t want to TPK my party due to the creature’s multi-attack.

The rest of the combat went well enough. The book The Monsters Know What They Are Doing has been an awesome tool. It gives you some realistic tactics for the creatures you’ll be throwing at the party. Since the idea was for Durnan to handle the Merregon while the party handled the Stirges, that’s where I focused my battle tactics.

Instead of having the creatures land and melee with the party, I had them fly around out of melee range. Then they would dive down and try to attach to someone to drink their blood. That was the only time the party could get melee hits on the creatures. On one dive, a Stirge successfully landed and attached to Viigo. This opened up an interesting opportunity. The next character had to roll to make sure that they didn’t hit their friend while trying to strike the monster. I feel like it gave it some interesting flavor without changing the difficulty of the encounter.

We then ended the session with the party receiving the mission from Volo (very much as written), the bar closing, and the party heading upstairs to get some sleep.

Session Takeaways

Incorporate more senses in environmental descriptions

  • I mostly described using sight and sound. That seems pretty standard for most people. But I should have gone in a bit more on smell and touch.

Improve battle preparation

  • I should spend more time contemplating the encounter. What leads up to it, what are some interesting wrinkles and what happens after?

Deepen understanding of the lore

  • I admit I'm not well-versed in Forgotten Realms lore. And that came back to bite me when I didn’t know the role that Asmodeus played in the world. That was a problem when one of the characters asked and I had to find a way around it. So going forward, I need to better understand the characters that are in play.