The Great Halloween Experiment

Let me take you to a party...

Last weekend, we held the Second Annual WorcesterShire Halloween party. As my birthday is on Halloween, I use these parties as an excuse to give our community something awesome, where I can get my favorite present - seeing my friends connect in weird and delightful ways.

I and Geof have been experimenting with how to make these parties as awesome as possible. Given that we’ve both run events for almost 15 years now, this is no small challenge. Let me tell you about our Halloweens - events where people leave saying, “That was the MOST FUN party I’ve ever been to”, where (this year) multiple people got engaged, fulfilled each other’s dreams, made blanket forts, and left hickeys on strangers. I’ll take you behind the curtain as well, to how the magic gets made.

Follow me to…

Kingdom Hearts: A Shire Halloween

For the Halloween parties, we usually choose a world. Last year it was “Dante’s Inferno”, inviting people to come as their shadow or their angelic selves. This year it was “Kingdom Hearts”, playing through different Disney worlds.

We started with the invitations.

We love doing paper invitations, because it’s just so sexy. Each initial attendee got one of these in the mail. Later, we expanded to a general Facebook event, but didn’t have much loss of buy-in/excitement because we still asked each person to fill out the QR form, and that set the tone.

The form asked questions like:

• "Why have you come?”

• "What do you seek?”

• “What can't you put in your face?”

• “What is your offering?”

The last question expanded:

All participants must bring a quest, riddle, offering, or challenge to offer other guests. (must play to play). You will be given tokens to award those who complete your challenges.

Imagine this as an open-world video game, where you are an NPC to everyone else. What strange quest will you send them on?

Need help? We created Questpool specifically for that reason... so go ask him! It?

Questpool, in the…flesh?

The form also included a donation request of $25-75. Most attendees filled it out, and most donated, which covered almost the whole party cost!

If there was an MVP question, however, it was this one:

What else are you offering?

Do you have other skills, performances, or gifts you would offer to our false idol Mickey and his universe of ne'er'do'wells? We have a talented community and we invite you to bring your unique flair to this collaborative universe.

Community Art

Here, I must digress to talk about art.

Community is an art. To bring the right people in, contribute to them as they need it (including helping them discover their own needs), and invite and encourage collaboration - that is a curation of personality as colorful as any painting. (Hint: the “right people” tend to be those who privilege contribution over complaint. But more on that in a future article.)

A good community, to me, also makes art. Sometimes that art comes in the form of support and empathy, sometimes in more tangible ways. It depends what the group has to offer.

Our community - such as it is; the definition of community varies, so let’s just say “the kind of people who come to our kind of party” - are a mix of Authentic Relaters, burners, and event producers. The latter two groups tend to be very useful and capable human beings. They are used to co-creation even of events that they didn’t create, and they appreciate the space to bring their art, when they are asked and feel equally invested in.

Thus, this party had the following offerings freely given:

• An electric cello and singing bowl sound bath, including all sound equipment brought in by the musicians

• A Cruella de Ville puppy-play strip tease by an international model and kinkster

• Several fire performances by professional performers

• Wall-projected Disney scenes provided by a videographer

• A Mad Hatter tea party including edible plates, a pianist, and strange challenges

• Ganshan tea service

• Hookah served by the Alice in Wonderland caterpillar (e.g. our housemate in a Caterpillar Tractors T-shirt 😂)

• Custom-order hot dogs served by ChefPool, aka Geof as a snarky Jewish deli-owner style Deadpool

• Bad advice served up for hours by volunteers in the back-porch Bad Advice Booth (courtesy of Facelazers, my Burning Flipside camp)

• Greetings coordinated by the White Rabbit, a Fairy Godmother, and two creepy Heartless

…plus hours and hours of setup and breakdown by friends and acquaintances.

ON TOP of this, there were the quests, many of which were elaborate. More on this soon.

The art that is community creates beautiful art, because most people love to give as much as they love to receive. The art is in the asking, the curation, the - yes - project management, because “just show up and do your thing” is far less effective than providing a run of show and keeping in touch with everyone.

If you’re creating an event, always ask what others want to give. Then, help them to give it, and be celebrated for doing so.

Cruella and Pongo

Now let’s talk about the part of the party that went over best of all: the challenges.

Bring Thy Own Fun!

I have to say, I was uncertain about this part of the event. Gathering and managing volunteers is high-touch - people opt in, you can keep in contact with them, and it’s okay if only a small proportion of attendees volunteer.

But asking everyone to bring a challenge AND a character? That’s chutzpah right there. It could have fallen flat on its face if nobody followed through. Especially since we planned to (and did) mildly shame people who showed up without a costume and/or quest by sticking Mickey Mouse ears and a “tourist” badge on them.

But the response was incredible. Here are some of the challenges people brought, copied from the Typeform (and I saw many of them happening at the party):

• I’m asking folks to find the lost princess inside themselves: a connection, or hobby, or part of themselves.

• I will hide 8 small sculptures at the party. If they are found the finders will be able to keep them and they will receive a song from me.

• I will ask people to change their Facebook status to “married” to another attendee (author’s note: I saw one person actually do this…and all the Facebook congratulations and confusion thereafter 🤣)

• At some point tonight, if not already, you will be met with an insecurity that resides stealthily within you. When you feel it, catch it, come deposit it to me, the insecurity deposit, and go forth, freed tonight from this pesky entity.

• Licensing fees! Participants must pay a licensing fee for their use of Disney likenesses, create and sign a justification for fair use, wear a disclaimer, arrange an "out of court settlement", or sign over a percentage of their tokens

• Rogue will try to tag you while maintaining eye contact. If you break eye contact first or she touches your skin, she gets access to one of your formative memories. If you choose to consent to a hug or other contact, Rogue will have to share one of her formative memories with you.

• I am Snow White who needs no prince. People will be asked to wake my from my sleep by making me laugh with a story or joke. In exchange I will give them warm apple cider

• I will ask "emperor's new groove" trivia and those who get it right will recieve a small artisinal llama from Peru.

• They must find something as of yet untold from someone else, and also a strange fact about a shark.

We handed out stacks of fake Disney dollars (meticulously designed by Geof, and then hand-weathered) for people to give to anyone who completed their challenge, and offered prizes for the winners of “most dollars”, “best challenge”, and “best costume”. The winning challenge was an elaborate quest that required ten people, who ran around for 30 minutes finding and smashing pumpkins that had yet more small quests inside of them, while trying to avoid the quest-giver (dressed as a witch) by huddling together and chanting a “spell” whenever she was close to finding them. It was epic high-investment fun.

The winning costume - Lumiere, with handmade lamps; his partner Belle; and their dog the Beast, complete with fur ruff and tiny horns. God I wish I took more pictures in my life.

Forcing attendees to be intentional about their contributions created self-selection. I had dear friends message me and say, “I can’t think of a quest or costume, so I’m not coming.” Because we were stringent about expectations, we had a highly invested group. An exclusive community creates an inclusive one.

Now, my friend. You have made it to our party. Step inside, and let me show you around.

Welcome to the Party!

You arrive to a quiet street about 30 minutes from Austin. After going through a yellow gate, you drive slowly down a forested pathway lined with lights.

To the left are “Parking” signs written in a Disney font. You park your car in a large easement, and get out. A character runs up to you - a white rabbit with a giant pocketwatch. “You’re LATE, you’re LATE!!” he cries. “Follow me!”

You follow the white rabbit down a driveway to a house. A giant, glowing tentacle protrudes from one window. On the porch you are stopped by a judgmental Fairy Godmother, who reviews your outfit.

As you have both an appropriate Disney character and a challenge, you are given a small stack of fake money and sent into the party.

Upon walking in, you see a room crowded with people dancing to a DJ dressed as a broom (from Fantasia), in front of stained-glass-papered windows beneath a giant wrought-iron chandelier. Behind the kitchen counter, a man dressed as Deadpool (aka Disney Jesus) is serving up hot dogs dressed with all manner of weird toppings, as he roundly insults the people across the bar.

You head to the right. Past the bathroom, there is a chill room covered in fake coral, treasure chests of sand, and AI-created tattoo’d alternatives of Ariel. Wave lights filter cool colors through the space.

Back to the main room. Someone taps on your elbow. “I’m the Hickey Mickey,” she says. “Want to do my challenge?”

You take her up on it, and find a consenting stranger who is open to receiving a hickey. Mickey gives you a dollar. Soon you are approached by another random attendee, this one dressed as a genie. “Want a challenge?” they ask. They have you write a desire you hold for the night on an index card. Then they rummage in their satchel and find someone else’s card. They point out who wrote it. “Your challenge is to fulfill that person’s desire!” the genie says. “I’ll give yours to someone else.”

After giving out some challenges of your own, you go upstairs. Music comes through the door at the top of the stairs, which has a doorknob that looks to be from Beaty and the Beast. You step in and find the floor packed with bodies, all lying on a floor completely made of mattresses, with lamps of branched wood and stone in the corners. A man is sitting on a massage table creating beautiful soundscapes with a portable electric cello and mixer.

Not wanting to interrupt, you head back downstairs. You notice another door past the kitchen. This one has necklaces hanging from it on pegs, each with a key as a pendant. The sign above it says “Mad Hatter Tea Party. Performances at 10/10:30/11/11:30. Take a key and come back when the room opens.”

Fortuitously, at that moment, they are opening for the next performance. You slip inside. In the room, you are sat at a giant table and handed a cup of tea. Underneath is a challenge. Yours is to make a blanket fort and caw at people who pass by. You oblige, as the room’s emcees break white chocolate plates and deal cards to everyone at the table.

You head to the back porch for a breather. There is a large yellow table and sign that say “Bad Advice Booth”. You ask a few questions of the person behind it. Their final piece of bad advice is for YOU to be the advice giver, so you trade places with them.

By the end of the night you have had so many wonderful and strange experiences that your head is spinning, even though you haven’t consumed a drop of alcohol. You have felt utterly immersed in the world of Kingdom Hearts.

Until next year…

The party rolled on until 5 AM for the last stragglers, long after I went to bed. The volunteer cleanup crew was up by 10 AM, and the house was spotless - floor mopped, dishes washed, furniture moved back, brunch made for everyone, and traditional cleanup crew photos taken with Geof’s “Let Me File That Under Fuck It” desk sign - by 1 PM.

In contrast, a friend hosted a party at our house the next weekend. Despite having half again the number of people, it was barely set up in time, had no coordinated breakdown, few activities, and left the house a mess. Still fun…but definitely not art.

Hosting our Halloween has taught me a lot about event design. It taught me that we have an incredible community and incredible friends, without which none of this would be possible. It taught me that a focus on contribution from ALL attendees, and a real expectation that it would happen, can create an explosive amount of energy. That it’s okay to go hard on a theme, especially if you put in the work of decoration and characters to make it real. That coordinated preparation and breakdown, begun far in advance of the party, is crucial for making it feel easeful. And that asking for help is where the magic begins.

Your loving Thought Dom,

Jiminy Cricket - aka, Sara Ness