Dimension 20

Adventuring Academy

Finishing a Campaign (with Molly Ostertag)

Season 1 Episode 6

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Brennan: Hi, and welcome back to Adventuring Academy. I'm your host, Brennan Lee Mulligan. With me today is an incredible friend, one of my oldest and dearest friends: she's a writer on “Owl House” for Disney, she's the author of the “Witch Boys” series, she's the artist behind the seminal, groundbreaking webcomic and graphic novel series “Strong Female Protagonist”, heard of it? Please welcome my friend, Molly Ostertag!

Molly: Hi!

Brennan: Yay! Hey, Molly, thanks so much for coming by!

Molly: Oh my god, I'm so happy to be here. I'm very excited and honored to be on your D&D podcast.

Brennan: And we are honored to have you. By "we", I mean me and Alphonse here. He's looking his usual perky self.

Molly: Why do you have to gender the skeleton?

(Brennan laughs)

Molly: They could be Elphaba, I don't know.

(both laugh)

Brennan: Well, Elphaba or Alphonse, we are so excited to have you; and, Molly, you hold the distinction of being the only Dungeon Master that has actually allowed me to play through and finish a campaign of Dungeons & Dragons! Oh my god, you did it!

Molly: I'm truly so honored to have that; and I can understand why it's a rare thing, because it was very hard to wrap it up. It was hard to just keep all you guys on track: people were moving across the country, people were getting jobs, people were getting caught up in stuff; and it's just like, I really, really wanted to make a campaign that I could see through.

Brennan: Yeah. Well, real life is a nightmare; and logistically, it's very unfair to all these wonderful fictional characters that are trying just to save the world themselves.

Molly: Yeah, they're just trying to hang out, and finish their stories, and get a conclusion to their narrative.

Brennan: Yeah, and then you gotta pick up and move to, you know, Washington or whatever, god!

Molly: Kaylee.

Brennan: Kaylee (laughs).

Molly: One friend who did that, love her very much.

Brennan: And yeah, I get it, it's your real actual life, but you could help us out. But that's so interesting. Other than the logistics of real life, which are very real; most DMs that watch this are struggling even to start a campaign, and I feel like it's so far down the line to think of the challenge of ending one, but it's actually a very real challenge, it's one of the hardest things to do. In Dimension 20, we've now shot a couple seasons of it, and it’s -- The wildest thing about it is how -- look, I have a lot of training and experience in running the beginning and middles of campaigns; the fact that I've ended three campaigns in the last year? Is crazy.

Molly: Oh, that's so cool though. I mean, I think it's -- You don't have to go into a campaign with the desire to have it have an end? It's also very admirable to just be like, "I just want to keep this fun thing going as long as it possibly can." But for me -- My favorite form of stories ever are books, and I just love a story that has a beginning, a middle, and an end; and I love how an end puts the rest of it in context, and gives you all these feelings, so I -- With our campaign that we played, specifically, I very much wrote that with the end in mind; 'cause I just knew that it would give it meaning, if we could see that we were heading towards this thing, and then if we sort of have this emotional last session it gives it the structure and meaning that sometimes I missed in D&D.

Brennan: Well, and I don't say this lightly, you're like a master of story structure; you love stories, and how they're put together, and what they mean. And one thing I wanted to talk to you about today, as someone who works on an animated show, but also has done comics - and we've talked about this a lot, because both you and I come from a LARP background, Wayfinder Experience -

Molly: Yes, we met when -- 13 years ago! I was thinking of it this morning. (laughs)

Brennan: (mock screams) Thirteen years, my god! Yeah, a long time ago! So we've all worked, you and I, in multiple different mediums of storytelling, and -- To talk about screenwriting, for a moment, Robert McKee has a great thing he said that really illuminated screenwriting for me, which was - and I think you would dig this and probably agree with it - which is: "Stories are not about their premises, stories are about their conclusions."

That, in other words: premises are great, and a lot of writers start with like, "Here's like, a fun beginning, or like, a world design that I'm thinking of," but really, the meaning we take from stories is about how they wrap up, how they end, what we take away from them; which really spelled things out for me, but in the context of D&D that feels really challenging.

Molly: Yeah, there's a good Kurt Vonnegut quote, I think, where he's like, "You should start a story as close to the end as possible." Which I really love; it should be the time when everything matters the most, the time when the stakes are the most heightened.

Brennan: Yeah, absolutely.

Molly: Yeah, I really get into it.

Brennan: Well, that's a weird thing - talking about the cross-pollination of different mediums - that's a note that we give in improv all the time, is: for your scene to be as clear as possible, for clarity's sake; start in the middle, don't start at the beginning. Which I think is really amazing, and people will sometimes get confused by that - and this is a cool thing to relate it back to D&D, and to our people watching at home - when you think about starting your campaign, think about starting your campaign in media res, right?

Molly: Yeah.

Brennan: Think of starting it, as the structures of the world are already kind of moving or beginning; because human beings are designed to pick up on context clues coming into the middle of something. If you're eavesdropping on a stranger's phone call and they have a 20-minute phone call, and you only get to listen to 30 seconds of it, where do you put your 30 seconds in that 20-minute phone call to have the best shot at getting what the conversation was about?

Molly: That's such a good way to think of it, yeah.

Brennan: And it's like, "Oh, the middle!" Because if you do the beginning, I'm just gonna catch this sort-of greeting, if I do the end I might miss a lot of context; but you go right to the middle and you catch some juicy bit of gossip right there, you'll probably be able to put a lot of pieces together. Cutting into the middle of like, "Look, I'm sorry! I'll get the carpet replaced! I'm going through a tough time at work!" (laughs)

You go like, "Oh, that's right in the middle of things, but I actually can kind of figure out what happened, just from this thing that we're starting with."

Molly: Totally. I think it's fun in D&D to be like -- I really encourage you guys when you're developing your characters to have backstories already, to be kind of like -- Like your character was, he sort of already had this thing where it was like, “The ocean swept you away from your home,” and he spent a year traveling with a carnival; and Noelle's character had a previous life doing something else, of being an actor, and then she was doing a second career, and it's just very cool to be -- Your characters are existing in a context, and they're existing in a world where things are already happening.

Brennan: Yeah, and where things change, and you kind of need that structure of beginning, middle, and end. So I would say for Dungeon Master -- One thing I will say that I loved about Pilgrimage, which was Molly's campaign that we all got to play in and finish, was the degree of finiteness and this kind of, I almost want to say it was almost like a deathly, a finality quality, some kind of a grave thing to it, which was, you're possessed by this demon, we knew it session two going in-

Molly: Well, the first session, I was just looking at my notes - because I haven't played D&D for like six months, so I wanted to remember what the last campaign I did was - but yeah, it was the first session: it ended with you guys all getting possessed with a demon, and it was slowly going to consume you, and then break out and consume the entire world, unless you traveled and did this huge pilgrimage to each of the six major god temples. And so it was very clear, and that's what you did! And it ended when you went to the last temple, and it was sort of like this suicidal road trip?

It just gave everything this real -- The characters, they had to stick together; and they had to think about their lives and think about, "Oh my god, this is the end of my life. This horrible thing is happening to me, and how do I cope with it?" And it ended up having all these really cool character moments.

Brennan: Well, I remember when I started to get the vibe of like, "Oh, this is going--"

Cause, we started on the temple of the god of Protection, went to the goddess of Love; and continuing that loop of the temples, I realized about one or two gods later, I was like, "Oh, we're gonna end on the god of Death. We're not all gonna make it out."

Molly: Yeah, yeah.

Brennan: Just like, “Ooh, that's a bad one to end on. This is gonna be rough." And it was so beautiful!

But, what I actually loved about that is: so much of my experience and time playing D&D was kind of set around - and the way that I DM is very sandbox-y, and very much like relying on the PCs, to put their kind of plot up, which I think also has strengths to it - but I was amazed at, in Pilgrimage, how much freedom I felt like I was given, by knowing what we were up to. The fact that the structure kind of existed from the beginning allowed me to take risks with my character that I otherwise wouldn't have; where I was like, "No, our quest is to go to these six temples: we might fail, we could get killed, this sort of evil, demonic cult could win; but we're moving along from place to place, and as we move along, we are changing."

And having that structure be in place let me take creative risks with the character, and make choices for them that were so rewarding and fun by virtue of having that structure.

Molly: That's really cool, that's really good to hear, 'cause I definitely had a worry that I would be imposing this thing - and it was like this demonic curse that gave you guys powers, it changed the way you looked - and I was worried that I was kind of imposing too much on the players; but I really did -- I think that everybody sort of took it and ran with it and made it their own story.

I was trying to explain - I was talking to somebody the other day about D&D, who plays it in a much more comedic way - and I was talking about how I love to DM, 'cause I'm not super good at writing comedy, I'm getting better, I'm learning how to do it at my job right now, but I really like to just do this very serious story, and to be like, "Here's the hard world that the characters can bounce off of." The characters are the funny ones, they're the ones that are rubber; but then there are certain parts of the world and certain parts of the story that are super solid, because it can give you something to bounce off of and to react to, and to exist within.

Brennan: I think that's so smart. I feel like that's very telling, too, and I think that what's wild is - I forget, it might have been Mike Mearls or somebody who was talking about this - who was making a point saying sandbox vs. railroad-style playing, neither of these are good or bad. They are both completely valid, and one of the things I actually liked about your campaign - and this is something to consider if you're a DM watching this at home who's thinking about creating a more railroad campaign, meaning the plot is there from the beginning - this is gonna sound funny, what I liked about your sort of on-the-rails campaign was: there was a reason within the world for it to be on rails. It was like, "No, no, check it out! You got cursed by a demon, here's the way to stop it; you're welcome to do what you want, but the world will end."

Molly: Yeah, and actually, the way that I first started thinking about the game was that I feel like people always make these really extreme characters, it's sometimes really hard to justify them all being together in a group, and to be like, "Okay, you all have to go to this thing," and it's hard to find a goal that everybody will equally want to do, and if they're having personality conflicts, to be like, "Why won't you run off and go do your own thing," besides that fact that you're all playing together, and you want to stay in the game, and so I just was like, "What's something that could bring everyone together?" and "What if you all have to stick together and do this quest, 'cause you're all cursed?" and that it's fun, I think it allowed for there to be these inner-party conflicts, because people were fuckin' stuck with each other.

(Brennan laughs)

Molly: Like, "I am so mad about this, and I can rebel against it, and everybody else in this world gets to do what they want, but we have to do this one thing," because the party is separate from everybody in the world by virtue of being the PC's, but to sort of give it a reason felt kind of neat.

Brennan: Yeah, it felt really neat too, 'cause I think what people resent about railroad campaigns is when the restrictions put on PC's abilities are born of out-of-game factors. So you're like, "Our characters are totally free to do what we want, let's not go to this dungeon, it makes more sense for us to ride north and try to get allies here," and then your DM goes...

Molly: "Uh, there's an earthquake, and a cavern opens, and you just can't cross it."

Brennan: You just can't cross it! And you begin to resent that,

(Molly laughs)

Brennan: Because you're like, "Well, what the fuck?" But I think that, actually, a railroad is really gratifying when it's supremely well-justified in the game, because that tracks to real life as well. Sometimes, you're in periods of your life where it's very sandbox-y -- and forget fantasy for a second, there are chapters of everyone's life where you're like, "Whoa, I'm really at a crossroads, I can kind of do multiple different things here, what do I want to do?"

And there's other chapters of your life where some outside event forces your hand and you are kind of forced to be reactive, and you're like, "Here's the situation as it exists, my choices are limited, here's what I can do."

Molly: Yeah, and your choice is how do you react in that situation? And there's so much interest in that, and so much interest of the character of yeah, if they're compelled to do something, do they rebel? Do they try to run away? Do they get angry? Do they come up with coping strategies?

Brennan: It was so beautiful, and that's the thing, too, is if you're really roleplaying as hard as you can, if you as a DM are encouraging your players to explore those inner things. The fact that our characters were always from the beginning bound to this curse and stuck with each other created so much of a focus, for me at least, on playing the internal life of my character; because it was this - and I've talked about this before on this podcast - but I've basically played this character that was this very peaceful, loving monk, spiritual character--

Molly: An island boy.

Brennan: An island boy, he was like a temple dancer, very sweet, good-natured monk/cleric. And as this curse befell them, and they started meeting gods, he just started to question the nature of reality; and then also, it was this thing of - and this might be because every character is fundamentally played by a player who can't escape themselves - but it was true that when I was playing a sweet, chill character who first encountered real evil injustice, and suddenly was like, "I can't be the way I've been," like, "I can't be relaxed about this, and I can't allow this to continue."

Molly: I would love to see you play a truly neutral character.

Brennan: A truly neutral character.

Molly: (laughs) I can't imagine it.

Brennan: What's weird is I've played evil characters before, and that's been fine.

Molly: But I'm sure that you've-

Brennan: I think I have an easier time playing evil characters than neutral characters.

(both laugh)

Molly: Well, it's so funny because -- This is what I love about D&D: because I'm a storyteller in a lot of ways, my biggest love is graphic novels, which I write and draw myself, it's very much just me; and I love the collaborate nature of D&D, because I am bringing in my brilliant friends who are all writers of some sort, and getting to play in these different styles, and I feel like my worlds are definitely -- Things are a little looser sometimes and - especially with morality - I'm just trying to mimic realistic things, but not always think out what's good and what's bad; and then whenever you play, you're always like, "That! That's bad!"

(both laugh)

Molly: And it's always -- I remember we went to the dwarf homelands, and I just had a throwaway line where I was like, "They have elementals powering mining machines," and you were like, "Slavery."

(Brennan laughs)

Molly: And I was like, "Okay, you're right, you're right, I really truly did not think beyond the image of a cool fire-giant powering steam-powered mining equipment," but you are always like, "I am thinking things through to the most intense, moral, logical conclusion."

Brennan: These are how systems of oppression propagate, alright?

Molly: I appreciate it, I appreciate it!

(Brennan laughs)

Molly: But it's so funny, I feel like all of my PCs are always kind of like, "I don't know, just do this 'cause I'm asking you to and I want you to do it," and like, "I'm sort of selfish."

And then you're like, "You're evil."

And I'm like, "Are they? They're selfish, I don't know.”

(Brennan laughs)

Molly: It's fun.

Brennan: Well, it's really fun.

Molly: It's a challenge.

Brennan: Well, I'm glad that I'm that PC, but instead of being like, "I'm gonna meta-game and get overpowered," I'm like, "I'm challenging the morality of your game."

Molly: Yeah, well I love it, 'cause it's like, I only have so much that my writing brain -- I have my interests and I explore them; and then to have people with different interests playing in the world, it forces me to explore that more.

Brennan: That's such a good point, that your PCs really do dictate the world, because your PCs are going to explore what they want to explore, and that won't match your interests as a DM. So again, for DMs that are watching this, when people emphasize improv, and the DMs have to have a certain degree of improvisational ability, what we're talking about is not the preparation is wrong or bad; it's obviously good, prepare as much as you want to, you won't be able to predict the lines of focus and attention and interest of your player characters, what they're going to interrogate will surprise you. For me, it's always going to be cosmology and ethics.

Like I remember - it's so funny 'cause I don't think you will think of this as a moment where you as a DM gave me the most fun thing - when we got to the Temple of the God of War, which was this giant colosseum bloodsport place, and this huge, fiery god of warfare and bloodshed and destruction, and I cast Detect Evil & Good on him, and I was like, "Is he demonic, or is he celestial?"

And you were like, "Celestial, he's a god."

Molly: He's a god.

Brennan: And I was like, "Okay, so that means that gods do not always represent what is good - because I understand this god is not good - but as a cleric I have to acknowledge that this god is necessary; which means my relationship to the idea of divinity has to become about gods representing not what is right, but what is true."

Molly: Which is funny too, because I feel like I was definitely approaching this world from a very Greek-myth kind of divinity where it's like, “Yeah, there are giant people who represent things, and will be as selfish and horrible as humans,” and you sort of had this more modern-Christian thing, where it's like, "Divinity is good,” and so, yeah, your character definitely came into it being like, "What is the nature of divinity?"

And I was like, "Well, they're large, and..."

(both laugh)

Brennan: Big, divinity is big size.

Molly: They glow? Lots of magic.

(Brennan laughs)

Molly: Themes, they each have a theme (laughs), they live in a big house. (laughs)

Brennan: Yeah, it's so funny to do the reverse of our world's timeline, where he was coming from-

(Molly laughs)

Brennan: -a kind of monotheistic place, and it was like, "No no, polytheism is where we're moving towards,” and it's a very pagan ideal.

Molly: Yeah, that was fun.

Molly: That was so fun.

Brennan: Well, I love that. Well, I also wanted to talk to you a little bit today about somebody that we've come up with a lot - that's come up on the podcast as well - We had Erika Ishii on the podcast, we were talking a lot about inclusivity in Dungeons & Dragons; and we've talked on the podcast before about how welcoming D&D, specifically like 5th edition, has been to the LGBTQ community, and I know that's something that's near and dear to your heart.

What is it about plunging into dungeons with your friends to collect treasures--

Molly: [laughs] It's just inherently queer.

Brennan: -and defeat -- It's inherently queer. Where do these queer narratives arise from?

Molly: It's so funny, it's been such a bloom in the last five years. I think, I was at Flame Con last summer - which is a LGBTQ comic convention in New York City, which is just the middle of the Venn diagram of nerd-stuff and LGBTQ-stuff, and it's a very big middle of that Venn diagram - and I was on their Dungeons & Dragons panel, and it was the most packed panel I've ever been on; people were just crowding in and standing around the walls, it was just so -- There is this really intense interest in it that I think comes from a lot of different places.

Definitely the language of 5th edition is really inclusive, in a way that it's just cool, when fantasy is very much like, "Yes, you are a part of this world," not like, "Sure, you can imagine yourself in it," but it's like, "No, you are, here are rules and here's writing specifying that queer people are in this world." That's really special, and I think it's really compelling to try on identities and try on characters. I think everybody likes that, but I think it has a special interest for people in the queer community: to get to experiment, to be like, "What do I find compelling? What feels right for me? What is fun to play? What is a model that maybe I could be like in the future?"

Brennan: I think that's huge. Well, we also both -- Our LARP background, specifically, is also much like D&D 5th edition; but in this case, an actual camp, an actual community-

Molly: Yeah, physical summer camp.

Brennan: -is incredibly inclusive, and extremely beneficial for a lot of kids that come out there that are LGBTQ. It's both wonderful and amazing to be like, "Whoa!" When I was 14, this hobby was not as inclusive as it is now, but suddenly it has become more inclusive, you go, "Oh, of course, obviously," for the same reason that so many of our LGBTQ kids at camp value this experience; because literally, we are saying, "Take this safe space to understand other identities, and therefore understand your own more."

Molly: -- I think it's the idea that identity can be a constructed thing. The idea that you can be someone other than yourself, or that you can present yourself in a certain way, it brings up a lot of ideas. I think the word "experimentation" can get a bad rap in the queer community 'cause it's used to dismiss people, like "Oh, you're experimenting," but in an ideal world you can experiment, you can try identities on and figure out what is compelling for you; and so something like D&D or LARPing is such a --

I have this story - and I know a lot of people who've had a similar story, where they played a gay or bi or however they identified, they played that character before they came out - and I definitely had that experience; and it was so meaningful, it was so good to able to be in this one very safe place in a basement with a couple of my friends. I will play as a gay character and it's so low-key, but it feels really safe.

Brennan: Yeah, I mean that's the thing: it's so safe, it's so low-key, it's a game, you got chips and soda and snacks, and you're just sitting at a table, but it's huge! And I think that it's something that is so easy to see the positive and the benefit of it, in terms of gender and identity and sexuality - and the truth is that's what the game has always been, though not as explicitly for LGBTQ issues --

Why do we play? Why do you pretend to be a hero? This is very corny to say, but: whoever you are playing these characters in these games, you are getting practice on doing the brave thing, and the selfless thing; and it stands to reason that if you can get practice being a hero, you can get practice being a queer hero, you can get practice being a hero that maps to an identity that you share.

The first season of “Fantasy High”, we had a character that had a mental illness, we had a character that was adopted; you're exploring issues of identity, and when you can do that through a character, you're given this safety, because it's not really you, so you can take bigger risks, they don't feel as scary, but then you're also learning! It's a crazy thing.

I think I might've told this story on the podcast before, but I remember being a - and 11 and 12-year-old boys are terrors on the Earth -

(Molly laughs)

Brennan: -and just a monster. Just, (imitates screaming) -- Really hyper, just stained with--

Molly: Terrifying, truly.

Brennan: Terrifying, but I was playing - and this is a really interesting thing too, talking about identity - my favorite PC when I was younger was Evia Darkshot: she was a tiefling fighter in a “Planescape” setting, she had bright red eyes, and horns, and long blue hair, reddish skin, and claws and stuff; and it was me playing a woman, which as a 12-year-old boy was like--

Molly: That's really interest-- was she your first character?

Brennan: She was my main-

Molly: That's so interesting.

Brennan: -She was my main PC.

Molly: Did you have a thought as a young boy, that you wanted to play a female character? Or was it a thought process for you?

Brennan: Yeah, I mean it was this weird thing where I - and listen, there were certainly some 12-year-old-boy things about it, 'cause I was like, "Let me tell you, this character? She's hot. She is really hot."

Molly: I mean, she's a tiefling.

Brennan: And there was a part of it-

Molly: We all know.

Brennan: She's a tiefling. (laughs) We're all there.

Molly: We're all there.

Brennan: - but there was part of it too, where I was just like -- Because the earlier characters I had made - I made a little gnome character who was a man; I made an Alaghi paladin, like a yeti paladin, who was a man -

And I just had made a couple characters, and there was a moment where I was filling out the character sheet and got to the part that said, "Gender", and I was instinctively going, "M", and then I was like, "Well, why? Why is that instinctual? I could be anything," and it was almost enough to tip me over the edge, the thought of, "You could, so why wouldn't you?" And it was so much fun.

Molly: That's cool.

Brennan: Of being like, "You could, so you should, you should try." And then, of course, I fell in love with the character, and played her for so long, I got her to 7th level - which in 2nd Edition is no small feat, that's a lot - she had a green steel longsword, like a Beytourian longsword, that burst into flame, but I remember --

Speaking about heroism as well, there was a moment where she - I think I might have said this on the podcast before, but in any case - this very sadistic DM had us -- We were trapped, surrounded by Modrons. There was a portal: the portal needed a portal key to be activated, and the portal key was a severed eye; and we were trying to rescue this young girl, and the DM had set it up like, "LOL, you gotta mutilate the girl, (imitates laughter)”

Molly: Is this someone that I know, the DM?

Brennan: No, you don't know this person.

Molly: Okay, okay.

Brennan: But they said, "You gotta mutilate the girl," and I saw the other players look around like, "What are we gonna do?"

And I just went, "Evia takes her clawed hand, reaches in, and pulls her eyeball out-”

Molly: No, ugh!

Brennan: "-and puts it through the door."

Molly: That's great.

Brennan: But I remember feeling something unlock in my chest, where I was like, "Oh, you can make the selfless choice, it's okay," and it wouldn't have occurred to me before; but seeing how scared everybody else was, you just were like… (imitates pulling eyeball out)

Molly: Oh my god. That's awesome. That's what I love about you as a player, because I think it's just so easy to be like, "Oh, they're just an NPC, it'll be horrible and gruesome and we can feel bad about it, but it's not one of our players," and so I love that you took a personal choice, not even to save another real human, but an NPC.

Brennan: This is a little girl, we're here to save her!

Molly: Yeah, you have to!

Brennan: You have to save her!

Molly: That's great, it's amazing, it's so cool.

Brennan: (laughs) And the DM was like, "I'm gonna give you minuses, you're not gonna as be as good at sword-fighting without your eye."

And I was like, "Cool, that's fine."

Molly: Get a cool eyepatch.

Brennan: I did have a cool eyepatch.

Molly: It's a win-win for everybody, honestly.

(both laugh)

Brennan: Oh man, I love that. I did change her character illustration to have an eyepatch, and I was like, "This has only made her cooler."

Molly: Yeah, that's really, really good. I'm gonna use that, that's fun.

(both laugh)

Brennan: But I love that. When you look back, are there similar - for PCs you've played, or NPCs - are there other things like that, where you see moments where you discover things about yourself or your identity? And I'll say, even though this is a D&D tabletop roleplaying podcast, even Wayfinder, going back to LARP characters...

Molly: That's a good question. Yeah, 'cause I definitely have DMed more at this point, and gotten more into DMing. Playing for me - funnily enough, I get really nervous in a way that I don't when I'm DMing, it feels really vulnerable - but yeah, Wayfinder, our LARP camp, definitely had a lot of those moments of just being like -- I was such a classic shy nerdy kid, and to just be those moments where you're like, “I can step out and do something, I can take an action, I can declare something loudly."

I remember we played a horror game once, which were always my favorites: where it was modern, it was a bus full of school-kids had crashed on the side of the road while a cult was doing murders in the woods; and it's basically a horror movie, but it is a LARP, it's the scariest thing. I can't do haunted houses anymore, 'cause they don't affect me-

(both laugh)

Molly: -because this is nothing, 'cause the LARPs were so scary. But I definitely remember that one: getting so into it, and so scared, and fighting so desperately for my life, and just having this thing of -- it was a very profound experience to just be like, "Oh, I would fight this hard if I had to, I care very much about being alive and helping other people, and just trying to--" I don't know, it's such an obvious one; but it's like you don't usually have an experience like that, where you have to genuinely fight for your life, and so I remember finding that really profound in LARP camp.

Brennan: Yeah, I remember there was those moments in LARPing, and D&D, wherever else, where you do realize: even though it's fake, it's just real enough to start to trigger parts of your subconscious, train yourself to react in certain ways --

There was a funny moment here when I first started working at CollegeHumor: we were having a big writers meeting, and it was I think my first week here, and someone said something like, "If the zombie apocalypse happened, I'd kill myself. (imitates laughing)"

And someone else was like, "Oh yeah, if the zombie apocalypse happened, I'd be done right away."

And there was a little lull, and I went, "I don't believe any of you. I think if the zombie apocalypse happened, you would all find a taste for blood,"

And everyone was like, "Jesus Christ, Brennan."

And I was like, "No, I think that we like to joke about how soft we are; we're actually not that soft, even the soft people are not as soft as they think they are. When it comes down to it and your friends are in danger, you will be amazed at the strength you have within you," and I think that that's something roleplaying games can bring out in us.

Molly: Definitely, yeah. I think another thing from D&D, that's less a character trait but just a skill of myself is: when I started DMing, I started doing it 'cause I moved to Los Angeles and I didn't know a lot of people, and it was a really good way to meet people and bring a group together; and it was the scariest thing to me. It's so scary.

I was just a writer of comics at that point, I was used to having this really solitary creation process; where I'd go away, and then after a year here's a fully finished book, and now people can read it, nobody could read it before then. And so, to me, writing and coming up with stories, it was just this intensely solitary process; but I really, really wanted to make friends, and so I was like, "I'm gonna try to do it."

And it was just so cool getting into DMing, and realizing that I could come up with stuff on the spot, realizing that you guys would throw curveballs at me, and I could take them and keep a poker face and come up with something totally on the fly, and that was something I sort of thought I couldn't do, and then just being socially motivated to do it.

Now I work as a writer and I'm in a writer's room, and it's -- Like that's my favorite thing ever, 'cause it's just D&D all the time: you're just coming up with ideas and you just have to throw out a million things and see what sticks on the wall; and it's this level of confidence, it's a confidence in that even if I don't have a billion stories prepared, even if I don't have extensive notes on this campaign, even if I'm going into a story-breaking session on my show, and I don't have a ton of ideas, I can trust in my brain that stuff is going to rise out. It's a really cool muscle; I never used to have it, or I wasn't confident in it, and I feel like I really got it from DMing.

Brennan: That's so beautiful.

Molly: (laughs) I know!

Brennan: It's so beautiful. You guys gotta play this game, you will-

Molly: Have you heard of it?

(both laugh)

Molly: Dungeons & Dragons.

Brennan: It's very fun. We're going to move into some questions: these are from fans of the show on our Discord server, dropout.tv is the website, if you sign up there, you can go and head over to our Discord server; also, if you're watching this podcast, you're probably watching it two weeks after all of our Dropout subscribers already got to see it, so why not head over to Dropout? This first one is from Marlyle (Colin),

Molly: Hi, Colin.

Brennan: Thank you, Marlyle. Hi, Colin.

"A common piece of DM advice I hear is to occasionally 'fudge' dice rolls, and basically lie to the players, in service of making the confrontations feel more dangerous and/or balanced. How do you decide when to let the dice rule supreme vs. stepping in to make the story more entertaining for the players? Do you approve of the ethics of fudging dice rolls?"

Woah.

Molly: It's a loaded question.

Brennan: Very controversial question. Loaded question.

(Molly laughs)

Brennan: Okay, this is really interesting.

Molly: I know, I feel like we have different feelings on this, and I'm curious to hear how you do it.

Brennan: Here's what I would say: there are a lot of tools for you as a DM to use, before you get to the need to actually fudge a die roll, right? If someone has not been successful in a long-term battle, and you can see that it's ruining their experience of the session: you can decide to give them advantage. If someone is on death's door, or you're worried about something: your NPC's can make a choice.

Sometimes DMs will be like, "Oh, if a monster knocks somebody down, they should go in for the kill every time; and if you don't, you're ‘taking it easy’ on your player characters,” and you go like, "No, the monsters are prioritizing active combatants vs. people that are unconscious; that makes sense, that's what you should do in a fight.” So there's a lot of ways that you can steer narrative without having to fudge die rolls.

I would say that for the most part - and I also am someone that likes to roll in front of the board a lot for big important rolls, which means I literally can't fudge the die roll, because it's happening in front of people, like the Box of Doom on Dimension 20 - but I would say that yeah, the threat of the dice needs to be very credible. I'm sure that DMs that I have played with have maybe fudged a die roll here or there; it doesn't break the whole continuity of the story, doesn't break the reality of the world to do it extremely sparingly.

But what I would say is: there are very few things in the game that are as precious a resource as the authority of the dice, and the player's understanding of the risk involved with their decision-making; and if that feeling of truth goes away, you are sapping actual real joy from the players. If you fuck up the dice too much, if you're too weird with the dice landing as they are, people start to go, "Oh, we're not really taking real risks," and then some of the joy goes away. That's my feeling.

Molly, how do you feel?

Molly: That's interesting, yeah. I feel super-comfortable fudging everything - but I feel like I've only dipped a toe into the online-D&D community, I know there's always a lot of discourse - but I feel like what's special about D&D is that everyone -- It's just a thing you do in your home, so it's like you can do it however you want. I understand what you mean, they are sort of the physics of the world a little bit; so you do want it to be realistic, and you want it to have this feeling of danger. You want to feel like, "Oh my god, they might roll a 20," or, "They might roll a 1," and these interesting, dramatic things will happen; and so I try to preserve it as much as possible.

But I also think it's a question of, "What are you doing with D&D?" Are you interested in creating a realistic sort of scenario where it's already figured out? And it's a very solid world that the characters are moving through - almost like a video game? And that's totally valid. My personal interest is more to tell a narrative; and so over everything else, I prioritize pacing, and so I think it's like --

This is almost less for dice and just more for preparation in general - where I see people getting very stressed by, "How much do I have to prepare?" And, "Oh my god, I have to draw a map of every single building they're gonna go to," and all this stuff, and it's like, you can sort of just go with the flow and listen to your narrative instincts; and be like, the thing that happens next is the thing that feels, narratively, like it should happen next in the story. Does that make sense?

Brennan: Yes, absolutely. I do understand that mindset, and I -- It's interesting, I would say that there is -- Let's be honest, there's a price you pay for fudging rolls; and again, I don't think any DM is saying, "Fudge a ton of rolls," you're talking about very specific moments where your story would potentially get fucked.

Molly: Yeah, sure, it's a time where it's like, "Is this going to kill a character because of some random -- Did the dice roll shockingly well and you're going to kill a character at a time when it would be really narratively-”

Brennan: Unsatisfying.

Molly: “-strange," yeah, just unsatisfying is the thing; 'cause that also takes away from player joy, if it's like, "Yeah, you were killed by a goblin who fired a weirdly good arrow." (laughs)

It's like -- If in “Lord of the Rings”, Legolas was taken out by a fucking goblin who threw a rock; and you're like, "Well that's not how Legolas is supposed to go."

Brennan: A hundred percent. I will say this: So the price you pay for overly fudging rolls is that risk goes away; and that your players - if you have players that are of a mindset of, "Hey, the dice are more like an aid than they are an authority", that's totally okay - If you don't have players that are like that, I would say that you really do run a risk of suddenly them going like, "Oh, if you're willing to subvert the rules to get the story where it needs to be, why am I bothering to think strategically or to fight hard? Why am I bothering to take these risks seriously? If we're just going to fudge stuff to make the story go along, then why don't I just kick back and take a nap and you tell me when we get to the end?"

You know, there is that element there -- That's being very extreme, but there is an element where it's like, "Oh, part of my ability to engage is the understanding that--”

I will say this: part of the ability to engage is part of an understanding that the Dungeon Master and the dice actually kind of have a good cop/bad cop relationship, which is how I like to think about it: where when I set up a battle, once the minis are on the table, once the fucking boss comes out, and the huge figurine is out there, then I as the DM go, "Guys, I'm sorry, it's out of my hands, I'm basically a ref at this point," and then it's like, if you want to tell someone you have a problem? Talk to the dice, and the dice are not going to be empathetic to your concerns about your character's story. What does that create? A feeling of real danger, which is fun.

That being said, I think that there are different rules for this in different places, and there's different levels of fudging die rolls, right? So if you roll in front of the board, obviously you can't fudge it. If the PCs have seen it, you can't just say, "No, ignore that, take it away."

If you're rolling behind the board - obviously, why do we even have DM screens? - nominally, the reason that there are DM screens is so that you're not tipping your players' hands to the level of bonuses, or what results are happening from which rolls, or how much damage you're rolling, et cetera.

Molly: And it's very ominous to hear the clattering of the dice.

Brennan: Very ominous.

Molly: When you hear a lot and you're like, "Oh no."

Brennan: Exactly. But there is something to be said for -- Let's say that you have a number of enemies facing everybody, and you have four enemies that are there; roll all four that are saving throws, and then be like, "Okay, two of these saving throws fail, two succeed; I'm gonna decide that these are the two that fail," that's not really fudging a die roll, but you're rolling and portioning narratively: where do I want the good saves and the bad saves to go? There's stuff like that where I think there's some give-and-take, where narrative and harsh consequence can meet; because I'll say this: as much as there is the threat on the one side of stakes and danger going away, you do pay a heavy price on the flip-side for never fudging a die roll.

I had this villain in this campaign I was running with a bunch of CollegeHumor cast members, where we had this badass hunter who was this demon-masked archer, who was firing from half a mile away; and he was super fucking scary, he was supposed to be a villain forever. The first time they encountered him: it was a cliff, they were in a valley with cliffs over them at sunset, and the sun was setting over the cliffs, and the arrows were coming-

Molly: Oh my god, that's so cool.

Brennan: -from the setting sun, so they couldn't see, and it was dealing -- And they were falling, there was poison happening, it was very, very scary. They spent two hours of real playtime planning a trap, they rolled incredible, my guy rolled bad; and I had to, after the first session that he was introduced, be like, "You catch him and he's dead," because they did it, they got him. Now, they fucking loved that; and weirdly, it was narratively unsatisfying, but in a way that they loved.

Molly: Well, also, if they put the effort in, yeah. I think it is just like being in tune with your players and understanding; if you have players who are really crunchy, who get really into the numbers, then yeah, the dice have to be very respected. And I do - I agree that you want consequence and danger to feel real, I think it is just -- There's so much math involved, and it put me off of playing 3.5; I was just put off by just being like, “That part is not fun for me. I want to play a cool story with cool characters, and solve mysteries and puzzles, and talk to people, and uncover interesting stuff," and so it's just knowing what you as the DM and what your players find the most interesting. Yeah, I think that there sometimes is room to, if people are more character and story-motivated --

Brennan: I totally agree. What I will say is this: I think you don't need to fudge die rolls if you are willing to have your story take really weird turns, because the dice are not necessarily really good writers. So if you feel like doing a lot of extra legwork as a DM to fix moments where the story takes a sudden bizarre turn, it's cool to have that amount of integrity for the rules. If you do not feel as confident in your ability to take weird haymaker punches to the jaw from the dice, and a moment comes up where you've rolled behind the screen - you're looking at something and you're like, "Oh, this is total-party kill," or, "This is my villain getting captured in a way that now, the campaign is over," or these moments - for me, I would try to solve those with storytelling; if you don't feel confident in your improv or your writing ability, I think it's okay. Every great once in a while, you cheat to--

(both shush)

Brennan: -to do what you gotta do, but work on not having to.

Molly: Yeah, but that's a whole other thing too; where of course you can prepare brilliantly, and it's also: how much time do you have to prepare? How much can you build the NPCs out? You cannot build an NPC as thoroughly as each PC is built, so you cannot give them the full set of abilities, so it’s like, even if they have really good stats, they don't have this real wealth of abilities that PCs have; and so I feel like that's tricky too, where it's - your hunter character, your villain, if you'd had the time to build him as lovingly as everybody was building their PC, he probably would've had more things to help him escape from a trap-

Brennan: A hundred percent.

Molly: -and help him avoid stuff like that, and so that's always tricky to me too. I feel like people get so intimidated about DMing, that I'm always just like, "If there's a shortcut that's easy for you, don't feel bad about taking it," whatever sort of serves having a good time with your friends.

Brennan: I totally agree. This is from Maya the Inferno. Thanks, Maya.

"How do you come up with names for characters, places, deities, et cetera, that are creative and meaningful?"

Molly: That's fun.

Brennan: That's a very fun question.

Molly: Yeah, for the campaign I just ran, I had a full list at the beginning; I went through and just generated a huge list of human names, dwarf names, elven names, city names, which was really fun. Because then whenever I needed something, I could just pop over to that document and grab something from that; and so I found that incredibly useful, because you will need to come up with names on the fly, which is always really difficult to do, and ended up with an elf named Gary at one point in our campaign.

(Brennan laughs)

Molly: Poor Gary. He was hypnotized, his family was kidnapped. It was very sad.

Brennan: Very sad, I remember Gary. I named an elf in my campaign Horizon, that I ran from when I was 12 to 17, I named this elf --

And one thing, just a heads-up about names in general, is that in our real world, names are rooted in the languages that produced them, right? So names are connected to a culture, and that culture has a language; which means there's always the potential for cultural appropriation. You should watch out when you're building fantasy cultures, not to harmfully appropriate from real-world cultures and fetishize or exoticize them; but what you'll see in a lot of world-building, even in the Player's Handbook, is like, "Oh, we tried to make names from a given land or people, use the same faux names, sound similar," you know, it's the thing that lets you know that someone named Tordak or Ragdor is probably a dwarf, and that someone named Milo Bittybottle is probably a fucking halfling or whatever, right?

So I named an elf in this campaign: it was using elven faux names, it sounded like an elven name - I had never said it out loud before, I just wrote it down - and he was the assistant to a dragon. I'm gonna spell this elf's name for you, and you can see the trouble I got into. The way you spell this elf's name is: F-A-L-A-S.

Molly: Uh-huh.

Brennan: F-A-L-A-S.

Molly: This is so funny, I did this exact same thing--

Brennan: You're kidding!

Molly: Not for D&D, but for a novel I wrote once when I was a kid; literally the same thing, I showed it to my dad and he was like-

Both: "You might just want to change that name."

Brennan: I didn't realize it until literally they were on-

Molly: That's so funny.

Brennan: -the deck of the ship; this silver dragon was speaking, he had his elven sorcerer assistant next to him, and he was like, "Very well, you heroes have done exemplary this day. Now for me to return home. Come, Falas!"

And I went, (gasps), and everyone exploded into laughter; and I went, "What?"

And they said, "His name is 'phallus'!"

And I was like, "Oh no!"

Molly: Oh my god.

Brennan: And it's like, "No, it sounds elven! Those are elven sounds!"

Molly: (laughs) Say it out loud.

Brennan: Say it out loud.

Molly: Before you say it at the table.

Brennan: First trick is: say it out loud.

Molly: Oh my god, that's so beautiful, I love that. Yeah, I think it's fun too, 'cause it's just -- I think maybe this is just me being a lazy DM or something, but the real world is so random and complicated that sometimes an element of randomness or complexity or things that don't make obvious sense is okay.

We grew up in upstate New York: there are a lot of cities with Native American names, there are a lot of towns with Dutch names, there's all these different cultures that come together and mix, it's not like one uniform thing; and so recognizing that it can sometimes add to the complexity of your world. If there is a dwarven town named Tyrandial and you're like, "Wow, what's the story here?" Like maybe elves settled it or something, you can kind of let your world - I feel this with all fantasy, not just D&D, but books and movies as well - let your world be as complex and random -- Like if you took anything from this real world, and tried to explain why it was this way? Why is New York called, “New York”? Why is it a new version of a city somewhere else? Why is that city called “York”? Could not tell you. You can allow this element of weirdness to give your world texture.

Brennan: I think that's really fascinating, and what's interesting about this is a question about names has immediately become a conversation about history, which is, I think, unavoidable. One of my favorite factoids is basically - in English, I think it was my mom or a professor, someone was telling me about this - history is so deeply woven into language, inescapably - and by history, of course, we also mean politics; the politics of the past continue into the politics of the present and the future - but that it's all woven into our language, you can not escape it; which is always frustrating when people are like, "Why's it gotta be political?"

And you're like, "You fucking ding-dong!"

Molly: It all is!

Brennan: “Everything's political, it always is!” But what's interesting is with this setting they'd be talking about: in English, the English language, the words "cow", "pig", and "chicken" refer to the animal; whereas "beef", "poultry", and "pork" refer to the meat, right? From those animals. Why are there two different words? Well, not only are there two different words for each, they're from different languages: "Cow", "chicken", and "pig" are Germanic; and "pork", "poultry", and "beef" are French. Because in England, during the time of the Norman Conquest and Norman rulership, the people tending the animals were Saxons and Germanic folk in the fields; and their aristocratic lords were Normans who spoke French.

Molly: Oh my god, that's amazing.

Brennan: It's like politics and lived-life and the facts of how your society is structured create the language you speak, and then of course the language comes back and reinforces elements of that culture, right? So when you're thinking of names for your D&D campaign, I think something to kind of make peace with is: what are you trying to do when you're making a name? You're just trying to create a feeling, right?

Molly: Yeah.

Brennan: So you're gonna try to -- What's a good name for my wizard character? What's interesting is history and politics is going to make its way into that, because what are you going to name your wizard? Quentin, Niles, you know-

Molly: Radagast.

Brennan: Radagast, right, something like that. You're either going to refer to Tolkien, or you're going to create some kind of aristocratic, British-sounding name, right? And it's very interesting because everything about the way we feel about things is based on real-world culture and history. It's really hard to escape from, I think.

Molly: Yeah, and it can be very -- It's interesting in D&D, which can be such a stream-of-consciousness as -- You're really just trying to come up with stuff on the fly; you're drawing from this, all of your cultural stores, a lot of which is full of these biases and stereotypes and tropes - which are not all bad or harmful, but they are reinforcing stuff - and so yeah, I think it's fun when you're coming up with stuff to sort of re-examine where you're getting your ideas from; if something just bubbles up, as like, "This is the right name for a wizard,” be like, "So why is that?" And, "What would another, more interesting name for a wizard be that you wouldn't hear somewhere?"

Brennan: Right!

Molly: And then that can kind of suggest a more interesting and unique feeling to your fantasy world.

Brennan: A hundred percent. So, examining biases, creating cool names for people; and it's really interesting too, because there are elements of trope that you're acknowledging, whether you are fighting them or accepting them, you know what I mean?

Molly: Sure.

Brennan: And some trope is necessary for things to work. You go watch the old “Lord of the Rings” movies, and you're like, "Look at how the elves are all speaking in RP." It's like Received-Pronunciation British, so it's like, (English accent) "We are the elves, we speak in this manner, we are the good guys," right?

And then these orcs are like, (Cockney accent) "'Ay there, lug! You lookin' at me, I'm speaking wit' a cockney accent!"

And you're like, "Yeah, I hate the lower classes as well!"

Molly: Yeah, I know. (laughs)

Brennan: And you're like, "Oh no!"

(Molly sighs)

Brennan: But the flip-side is true too, because someone did this cool etymology thing with me, of: if you're going somewhere, and you have an invitation in your hand, would you rather go to a place where you've been promised a “hearty welcome”, or would you rather go to a place where you've been promised a “cordial reception”?

Molly: Hmm.

Brennan: They both mean the same thing; but for me at least, I'm like, "Ugh, ‘cordial reception’? Fuckin', I won't be able to touch shit, it's gonna be cold; no thank you, I'll go to the hearty welcome."

Molly: Cut to me going home, rewriting my wedding invites.

(Brennan laughs)

Molly: "Goddamn it!"

Brennan: "Goddamn it, oh no!"

Molly: "Brennan's not gonna come!"

(both laugh)

Brennan: But there is an element of cultural bias, even in that. So when you're creating names for your PC's, I think look at your favorite novels - fantasy novels - think about the feeling you want these names to evoke, but when you're also thinking about the fact that different names and languages evoke different feelings, different sounds evoke different feelings, why is that, right? And examine that a little bit, why?

Molly: Yeah, and you can make a wizard who is just the most classic, wonderful wizard with a long, gray beard who's named Quentin, or you can sort of put your own spin on it; and I think that often, at the table, that leads to creating more of a interesting community where you guys have your own icons of this world, your own tropes that exist in this world that I think can be really, really fun. That's what I love so much about D&D, is that you can just make this world that is so separate from our own, and you can really just play in it.

Brennan: I love that so much. I really enjoyed that the advice I thought to give for this question about how do you name NPCs was: "Deeply contemplate the ethics of everything that you're doing, to the point where you feel like--” (gasps) someone probably just wanted something simple, like, "Ay, you can look up a names book!"

Molly: Google a names generator, (laughs) there's a lot of them out there: elf-name generator, dragonborn-name generator; they're all there, it's so helpful. Make a big list, that is genuinely so helpful.

Brennan: Yeah, if you don't wanna go on a long journey of the soul in examining which systems of oppression you're complicit in, go find a good name generator online. Wonderful! Guys, this has been such a wonderful talk. Thank you so much to my guest, Molly Ostertag,

Molly: Thank you for having me, this was great!

Brennan: We had a wonderful time here on Adventuring Academy, and we'll see you guys next time!

Both: Bye!

Captions extracted by: gluegunshots

Edited by: gluegunshots and Liviathan