Hello, how are you? Would you like to engage meaningfully with me? How do you feel about this as-personal-as-you-want-it-to-be, non-threatening, question? Those are the hallmarks of a good ice-breaker, and these are the best ones I've created or pilfered in the past three years.
At the SOAK festival in 2016 I suffered back spasms from an extended Butoh session, and in order not to spoil that last night I made a game of laying still in one public location from dusk to dawn. As I needed to entice people to keep me company among the night's many attractive options, this little ditty came to me. What works well about this question is its luxurious layer structure. It can't be answered monosyllabic. Thinking about the constituent parts creates an unwinding, an unraveling that the answerer doesn't necessarily need to know completely before starting. In this way the speaker can dollop out pieces of their personality slowly, which each layer a revealing different inner self. It's an act of additive creation—much like a burger.
At the SOAK festival in 2017 I suffered a herniated disk jumping off a tall novelty-wrestling platform. Again I needed to lie down for the majority of the night, and had ample opportunity to review my anxiety of recently dropping out of my PhD program. I wasn't going to be a Doctor of Philoshophy, but, feeling limitless I wondered, could I be another kind? The term 'philosopher-king' came to mind, but it wasn't right either. 'Philosopher-athlete?' 'Philosopher-artist?' 'Philosopher-barista?' The beauty of this question is that you assert your conversation partner is a fully-fledged and self-labelling philosopher. This means people have to dispell a pretension that you've foisted on them. It's a bit unfair, but if you're a bit familiar with your audience you can enjoy play of squirming together.
Since I didn't injure my back at SOAK 2018, I was on the lookout for new ice-breakers. I always knew it was possible to do it this way, and so and was relieved to discover one without bodily harm. I met a like-minded enthusiast of ice-breakers in my new boss, @natematias, and I knew I could trust him after he asked this question to open up our very first meeting. He'd just shared a photo of a storm he was in the day before, sailing in Boston. Was there a particular storm I remembered, he asked? This question gains it's power from the storm's power. The vividness of the memories that this question can invoke makes for potent material, impossible to fumble as a storyteller. That's what you'll get out this question, a surefire story of fear, wonder, or intrepid adventure.
If you use these icebreakers, or feel like answering them, report back to me at @notconfusing. Happy breaking.