The Thrill of the Ask: Business Lessons from the Cuddle Party

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By Cass King, Groundswell Social Venture cohort member

“Did you tell me we were sleeping in a tent?” I asked my husband, in a voice which he interpreted, correctly, as: “You totally did not tell me we are sleeping in a tent.”  I’m not much of a camper, but I really took issue because our destination was Manhattan.

“It’s supposed to be nice…” John began “It has a mattress.” I can’t imagine what my face was doing at this point, but I’m sure it wasn’t good. “Well, anyway” he continued “It’s really kind of Sahara to offer us her backyard”- I scowled, imagining a backyard in the Lower East Side “for free”. Sigh. Well, there was that.

“You’re here in time!” Sahara squealed as we arrived, dragging our tired suitcases into her tiny painter’s studio. Her bed took up the whole floor and her paintings covered the walls. “Grab these.” She floomped a huge pile of blankets into our arms and hustled us out the door before we could take our boots off.

Across the street at the LGBTQ center, a party was about to start. It was a Cuddle Party, “A playful social event designed for adults to explore communication, boundaries, and affection”. It seemed to me, a certifiable introvert, like a social event designed by sadists to explore sadism, sadistically. I imagined myself, skewered like a bug on the pin of my profound discomfort, being spooned by a stranger. But what could we do? Our host was throwing the party, we could hardly decline.

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Inside, pajama-clad adults gathered in a circle on a patchwork of futons and fuzzy pillows. What followed was a workshop that radically changed my viewpoint on asking for what I want and dealing with the answers.  Leading the workshop were relationship counselors Marcia Baczynski, a thoughtful and enthusiastic nerd with a mop of curly blonde hair, and Reid Mihalko, who was kind of like a cross between a quarterback and a golden retriever. I can’t tell you verbatim what they said, but some of the things I learned at that party were invaluable lessons in life and business that changed me in a deep way.

I learned, to my great relief, that we were welcome to engage with others or to just sit and read or sketch, according to our own needs and desires. I learned to validate my desires as real and worthy of attention. I learned that not articulating my needs and wants leads to resentment, hurt feelings and wounded expectations. Marcia calls this phenomenon desire smuggling.

So, will every desire and request be granted? Obviously not. In fact, one of the first exercises we did was to turn to a stranger and ask for something, only to have them say no. We were encouraged to say YES when we mean YES, say NO when we mean NO, and say NO when we mean MAYBE, and we were reminded that it’s ok to change our minds.

Learning to interrogate my feelings around rejection was so profound. I vividly remember Marcia imitating a five-year-old, knees bobbling as she pretended to ride a tricycle. “Hey, you wanna ride on my tricycle?” she asked Reid. “No” he replied. “OK!” She said and bobbled off to find another candidate. It’s an image that really works for me, especially when I’m reaching out for help or asking for someone’s time. I have to remember that receiving a “no” is just information, not a reflection on who I am as a person.



There’s one more magic phrase that I remember hearing, one that has really stuck with me. On hearing a “no”, we were encouraged to say “Thank you for taking care of yourself.” Isn’t that beautiful? A grateful acknowledgment of a boundary.

Reflecting on why I want to share this story with the Groundswell community, I think it’s because when we are trying to build a social venture, or any venture, we ask for a lot. We ask a lot of our partners, our friends, ourselves. We ask strangers for their time, we ask funders for financial support, we ask potential clients for an honest assessment of our ideas. And we hear things that we don’t want to hear. As entrepreneurs, we need to foster a resilience to rejection in order to keep working our ideas until they really, truly work for us and the communities we would like to serve.

So, when we can ask without demanding a favourable outcome, when we can hear a no with grace, when we can trust others to say yes or no to our requests, doesn’t that mean we can ask for anything? And isn’t that exciting?  Doesn’t that change our outlook from “It can’t be done that way” to “Why not”? And isn’t “Why not” the root of all social innovation?

I have to tell you, I got a lot more out of that Cuddle Party than a snuggle and a nap.



Back home at Sahara’s, we walked carefully through her hallway, where thick oil paint was drying on several large canvases. Through a screen door was a paved no-man’s land sliced between tall brick buildings, inaccessible from the street. At 500 square feet, Sahara’s ‘backyard’ was bigger than her apartment. Green netting camouflaged us from the apartments above, and fairy lights twinkled around an inflatable pool. There, on a raised platform, was a Burning-Man-meets-Old-Hollywood fantasia of a tent. Inside was a pillow-top California King mattress that would not have been out of place in a five-star hotel. Egyptian cotton sheets were like floating up into the next tax bracket. We climbed in gratefully as our host bid us goodnight.

“This is one of those experiences that money can’t buy.” John said sleepily. I agreed, reflecting on the privileges of this creative life. There, nestled in the crook of a true Manhattan story, I slept like a baby.


Cass King is a maker, a singer, and a sexual health and wellness nerd.

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