On Tabletop RPGs, LGBT Romance, and Storytelling: An Interview with Molly Ostertag

Pilgrimage art by Molly Ostertag

When it comes to infusing her stories with LGBT and gender non-conforming themes, writer and artist Molly Ostertag is no stranger.

Her most recent graphic novel, The Witch Boy, tells the story of a boy in a magical society who gains aptitude with spellcasting – despite the fact that all male-identified people he knows study shapeshifting.

Outside of comics, though, Ostertag is also an accomplished roleplayer. She’s been featured on the renowned actual-play tabletop series Critical Role, and has recently become the Dungeon Master of her own streaming tabletop RPG series, Pilgrimage.

In a recent email interview, Ostertag said she first encountered D&D as a very shy freshman in high school. “I rolled a Charisma check every time my character had a conversation because I was tickled by the idea that my character could be good at talking to people when I wasn’t,” she said. “I think I only played one session because, as I said, incredibly shy.”

Ostertag later developed roleplay skills at a unique LARP (live action roleplay) summer camp, and continued to delve into the world of Dungeons and Dragons in high school, where she developed her first lasting character, Aurelia.

Ostertag describes Aurelia as a half-elf paladin who “was very bad at figuring out the right thing to do, but very good at hitting. The campaign got intense – one member of the party ended up betraying us to his evil god, and we had to fight him, and multiple timelines were involved, and it was really cool!”

Outside of comics, though, @MollyOstertag is also an accomplished roleplayer. Click To Tweet

It’s always tough on players when a campaign ends — the bond created between those people who share such an intimate storytelling experience is like no other. Still, Ostertag said she still maintains these feelings toward her fellow players and the DM from that campaign, despite the story ending when she moved away from New York.

Perhaps most notably, Ostertag said she remembers how important Aurelia’s sexual orientation was to her at a time when she wasn’t fully out. As a gay character, Aurelia gave Ostertag “a safe place to quietly explore that part of myself.”

These themes are something she’s also weaving into her new Twitch streaming campaign, Pilgrimage.

Pilgrimage characters, from left to right: Humza, played by Brennan Lee Mulligan; Quorrin, played by Noelle Stevenson; Merriweather, played by Keely Weiss; Mochi, played by Lola Binkerd // Art by Molly Ostertag

Pilgrimage tells the story of four heroes who have absorbed part of a demon and gained mysterious powers in the process. The demon slowly kills them as they move through the world, and their only hope of survival is to visit all six of Faerun’s temples to receive blessings from the gods.

The catch? If they die, the demon will be released to consume the world.

Ostertag said she created this hook to give the players “a life-or-death reason […] to have to stick together, even if they had huge personality conflicts”, a common issue in both homebrew and officially-published Dungeons and Dragons campaigns.

Putting various player-created characters together without a clear path ahead can always be difficult, but Ostertag mentioned that a ‘found family’ theme has organically developed through gameplay in Pilgrimage.

“All these characters are very different, and they got angry and frustrated with each other a lot at first,” she said. “Over the campaign, however, they’ve come to understand and love each other like a weird cursed family, and have been deeply affected by their experiences. That’s all on my amazing players for exploring those character arcs and developing relationships.”

The Pilgrimage players have experienced various conflicts in their adventure, including starting a war, being pursued by a cult, swapping bodies, and revitalizing an ancient religion.

“We’re having an amazing time,” Ostertag said.

In-game, Ostertag said she finds it easy to incorporate queer themes and characters into her stories: “As a DM, I encourage my players to make their characters queer if it feels right.”

Hasbro subsidiary Wizards of the Coast, the official publisher of Dungeons and Dragons, encourages “queering characters” with the current Fifth Edition (5e) of the game, where players are encouraged to think more wholly about their characters and play people of varying genders and sexual orientations.

In an aside, Ostertag said, “Now that I think about it, I’m not sure if there have been any certifiably straight NPCs in our game at all…”

'As a DM, I encourage my players to make their characters queer if it feels right.' - @MollyOstertag Click To Tweet

It’s a sentiment I can recognize in my own home game as well – and something I really value in RPGs. For queer people, it’s extremely validating and welcoming to see players that look and feel like them in fiction, and this extends to stories we tell around a table (or on Skype) with our friends.

Of her own players in Pilgrimage, Ostertag remembers “the players had to help a man rescue his family, and no one was particularly enthusiastic about this bit of do-gooding. When they found the family, it turned out he had a husband, and everyone yelled at me that they would have cared much more if they’d known.”

She said she’s also interested in including romance storylines for her players, though finds that “it can be a little awkward to play it out at the table.” Nonetheless, Ostertag  said she still brainstorms ways to include romance, as most of her favorite works of fiction have included romance plots.

Fortunately for her, there are various game systems to tell collaborative stories in, and some of these feature romantic storylines as a key element.

'Now that I think about it, I'm not sure if there have been any certifiably straight NPCs in our game at all…' - @MollyOstertag on the Pilgrimage campaign Click To Tweet

Besides Dungeons and Dragons, Ostertag has also expressed interest in Monsterhearts, a game directly inspired by the experiences of queer youth.

Monsterhearts is an indie game run on the Powered By The Apocalypse system developed for Apocalypse World, one of the original indie tabletop roleplaying games. Players build paranormal ‘monster’ characters typically seen in supernatural stories, like werewolves or vampires.

These characters reflect the experiences of creator Avery Alder, and those of queer teens worldwide, who also often have to keep their identities a secret.

More: The Shape of Water: Desiring Monsters Is a Tale As Old As Time

In a February 2017 interview with The Guardian, Alder said, “I explored a lot of my own identity as a queer woman and a trans woman through games, and I wanted to create something about coming to terms with queerness.”

Alder goes on to describe how in various situations, queer people are made to feel ‘monstrous’. Monsterhearts deals with this topic directly, as it’s set in a high school. Players are encouraged to create queer stories for their monsters and play out romantic storylines with their fellow players right at the table.

Ostertag said she likes the idea of exploring teen drama in fiction, and says that she’d like to explore Monsterhearts someday.

She said, “I ran a D&D 5E campaign last year that was set at a high school for adventurers. It was fun but had some flaws – a static setting is surprisingly hard to pull off [in Dungeons and Dragons], or at least it was for me.”  Still, she said the “tiny self-contained bubble of high school” settings appeal to her.

For updates on Molly Ostertag and her work, follow her on Twitter. You can also check out her work, including comics, at her website.

For updates on Pilgrimage, follow the campaign on Tumblr.