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Natural 20

Tonight was the culmination of all our hard work. Years had been invested in this campaign as we’d each meticulously developed our characters level after level, adventure after adventure. We slogged through dungeons and slayed dragons. We amassed and spent fortunes, saved whole towns and destroyed entire cities, and all of it led to this moment where our adventuring party was about to face off with our mortal enemy, the Demon King.

I was fortunate to have found this online gaming group on Roll20, the online community that allowed us to connect with other gamers around the world to play virtual tabletop roleplaying games. I’ve always had a hard time finding people who share my hobby, as my social anxiety and extreme introversion kept me home most days. But in our campaign world that didn’t matter. I wasn’t Oliver the lonely customer service rep; I was Evindal the Exalted, an elvish cleric who had risen through the ranks to become his deity’s greatest champion.

Six months into the campaign, I was surprised to realize that one of the other players in the campaign lived in my city. Amaryllis, our party’s halfling rogue, was played by a girl about my age named Violet. We got to know each other during one game session when nobody else could make it, so the Dungeon Master had taken the two of us on a brief side quest. It was one of my favorite moments of the campaign and I really felt like there was a connection between us. We private messaged each other so much on Roll20 that we shifted over to our own Discord server to chat privately during the sessions.

Knowing that this might be our last adventure together, I resolved to ask Violet out. I couldn’t take the chance of letting this campaign end without at least seeing if there was anything between us, terrifying as the thought of putting myself out there may be.

U ready 4 this

Her message popped up on our private Discord server.

As ready as I’ll ever be.

U better pray 2 that god of urs

I have a plan.

An hour later, my “plan” had become a dumpster fire burning so brightly that I’m certain it was visible from the upper atmosphere. Thanks to our party rolling a number of natural 1s (“critical failures”), and our opponent getting lucky with a well-timed natural 20 (“critical hit/success”), The Demon King was on the verge of destroying all of us and enacting his evil plan to eradicate all life on the planet.

gr8 plan

I’ll admit, we’ve had some setbacks.

the corpse of our bard agrees

I have one more trick up my sleeve, but I’m going to need you to do your thing...

On my next turn, I called upon my deity with the most powerful spell I knew: divine sacrifice. My god would exchange my life for a massive slew of powers and bonuses that I could bestow on another person.

OLIVER NO

But it was too late. The spell was cast and my character had ascended to the afterlife. The only thing left to do was bestow my bonuses on our party’s thief. The one whose turn was next and could add these incredible stats onto her already staggering bonuses for sneak attacks and backstabbing, which she was already positioned for.

Avenge me

It worked! Amaryllis the thief backstabbed the hell out of the Demon King and destroyed him, saving the world and cementing herself as one of the greatest adventurers of all time. It was the destiny Violet had always dreamed of for Amaryllis.

bold move

I have my moments. Hey, um, speaking of moments... would you maybe want to meet up IRL sometime?

ooh another bold move

So what’re my chances?

gotta roll the dice to be sure

I triggered the dice-rolling app in our Discord server. The wait for the digital 20-sided die to cycle through its faces as it “rolled” was interminable, but when it finally came up on screen my jaw dropped as I stared at the “20” looking back at me.

critical success... how’s Thursday?

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