Some context about me before you start reading: I am OBSESSED with social spaces for social change. How can we design better spaces for meaningful connection, conversation, and change lives rent free in my head. At the time of writing, it’s my fourth year as CEO of Soapbox Project, which is a cozy community that helps people transform their climate anxiety into joyful action. In 2024, it’s shifting from mostly online into mostly/morely in-person and city-based.

I’m midway into hosting Soapbox Seattle, an IRL pop-up community center to see if this physical space thing pans out, so I am nonstop thinking about third places.

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Two of the defining characteristic of a third place are that they should be primarily a conversation space, and they should be playful.

Icebreakers have gotten a bad rep. That’s because most of them suck! I’m sick of two truths and a lie. I’m sick of trying to find a fun fact. I bet you are too.

With the loneliness epidemic causing real—even deathly—harm to society, more and more of us need to lean into our national human skills: community building.

We are born to do the work of connecting. It’s literally ingrained in us.

In his book Together, Dr. Vivek Murthy says something that boggled my brain:

We might not guess that we’re thinking about social connection all the time, but it actually occupies more time than we are aware. Another UCLA neuroscientist, Dr. Matthew Lieberman, has spent the past two decades using functional magnetic resonance imaging, or fMRI, to watch the brain’s activity when people are talking, hugging, solving math problems—or just sitting alone…What happens, he wondered, when we’re just kicking back and doing nothing? What’s our default network? The answer astonished him. “Whenever we finish doing some kind of non-social thinking, the network for social thinking comes back on like a reflex—almost instantly.” In other words: “Evolution has placed a bet that the best thing for our brain to do in any spare moment is to get ready to see the world socially. . . . We are built to be social creatures.” This means that we’re constantly preparing for our next meeting, love affair, confrontation. Even if we don’t realize it—even if we think of ourselves as profoundly introverted or task-oriented—we spend most of our time thinking about other people. To a large extent, Lieberman says, that’s because our relationships with other people define us.

One easy step to being a better connector: get good at icebreakers. First impressions matter, and there’s not much worse than entering a room full of people only to be greeted by awkward silence.

Every good event needs a reverse bouncer

When you go to a bar and see a bouncer outside, you know what to expect. You straighten your posture, show off your best behavior, and hand them your ID. There’s no confusion on what you should be doing with yourself.

When you’re hosting an event, the first person you meet matters. When you walk into a chocolate shop and you’re immediately offered a free sample, it only gets better from there!

Priming people to assure them they’ll have a good time is so important. In my mind, that’s what icebreakers can do. But all the conversation prompts in the world won’t save you if you’re not actively assuming your host/reverse bouncer/welcomer role.

When you prompt guests with a gateway activity, giving people something to do soon after entering the space, it creates an atmosphere and expectation of shared ownership. In other words, it becomes THEIR event, not just yours, and this helps the vibes hold themselves.

Virtually, you can do this by:

• Setting up a waiting room message, especially if you use a tool like Zoom (I saw one that said take a moment to breathe deeply and loved it)
• Chatstorming a vibe check (e.g. in 30 seconds, put ONE WORD on how you’re feeling in the chat)
• Putting a fun poll on the screen that sets the tone for the event
• Welcoming people with their names as soon as they enter, either verbally or via chat, especially if your event has less than 30 people. Saying “I’m so glad you’re here” goes a long way!

When you’re hosting an in-person event, have a welcomer. I usually take this role myself when I’m hosting something where I’m expecting new people. I hate HATE not knowing what to do when I enter a room full of strangers, and it really helps to have a friendly face who tells you what to expect and what to do next.

It’s not complicated—I introduce myself, take their coat/bags/stuff, offer them a sparkling water or something to drink, and send them to the welcome station where they can make their own name tags (and add fun stickers).

Just think of how you’d want to be welcomed when you show up to an unfamiliar space, both virtually or in-person. Those two minutes of thinking will affect the first two minutes of your guests’ experience and can make or break the vibes of your event.

Hosting is about listening and creating belonging

One reason I’m able to host such fun, vibrant, engaging events (don’t take my word for it — here’s a video) is because I pay attention to what people are coming for.

Before ALL the events I host, I have some sort of question in the sign-up form. Sometimes it asks people to rate their climate anxiety. Sometimes it asks what their dream vision for the future looks like. And ALL the time it asks for any accommodations we might add.

No one likes a party when the host is just showing off about their Stanford-attending son or how much their newest car costs. Our job, as good hosts, is to help people feel seen and heard. It’s to hold space in a way that matters.

Sometimes icebreakers suck because they make people uncomfortable.

I like discomfort. I like healthy conflict. But there’s a time and a place. The beginning of an event is not it (unless it’s a bootcamp or something, in which case you know best).

Some thoughts on comfortably tapping on the ice:

• Figure out what the goal of your icebreaker is. What is an icebreaker supposed to do for you? For me, it’s something that makes people comfortable in the space so that they can be courageous later on. All icebreakers I use have the goal of building a shared experience that shows the possibility of co-creating the remainder of our time together. They are essentially a gateway drug to more intense engagement 😉
• Have introvert- and extrovert-friendly activities. As an obnoxious extrovert myself, I got some fantastic feedback from more reserved friends. Now I know that not all icebreakers have to involve conversation! You can draw together or journal together.
• I beg of you please make it relevant. My hatred for two truths and a lie is that NO ONE CARES. Fun facts are slightly better, because they can spark some good conversation. But if your event is a French meetup, it’s probably more relevant to ask someone about their funniest language mess-up than it is to ask them to lie about their life. Think about what your event IS! Clear > clever when it comes to icebreakers. I’d rather be asked “what’s your proficiency in French” than a quirky irrelevant question that takes me minutes to think of.
• You must burn more calories than your guests. Hosting is energetically expensive. The best gatherings take the most work (at least the most brain work) from the hosts. You can definitely have activities that challenge people’s brains, but maybe keep the icebreakers light and easy to think of. Specific prompts are great (”what shows have you been watching” vs. “what’s your favorite show of all time?!?!?”).
• Give people time to think. Yes, I advocate minimizing the thinking time of icebreakers (see above) but also… things take time! It’s okay if no one responds in the first three seconds of you asking a question. My greatest skill I learned in the past two years is how to hold silence. It’s uncomfortable but it shows people that we’re all responsible for the conversations that happen in this space. I was in a welcome call for Dreamers & Doers facilitated by Seisei and I LOVE, LOVE, LOVED how she said which three people would go next in their intros. What a huge mental relief!

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Icebreakers I love that can be done virtually or in-person

1. Grab a physical object that makes you smile. In a recent democracy-related call I facilitated with my now-friends Camila and Marta, we posted this question in the Zoom chat: Welcome! While we wait to get started: go find something that makes you smile! and it was great fun. Someone grabbed their child, which was a clear winner.
2. Change your background to your favorite meme. No explanation needed on this one. It gets people laughing, and laughing connects us.
3. Draw a group mural on [a topic relevant to your gathering] For the Soapbox Seattle community center pop-up I’m hosting, one of our social stations is to draw something on a specific prompt like: draw the neighborhood of your dream future.

4. Say how your best friend would describe you I got this from Tatiana and I like that she sends it out beforehand. It’s a deep one! It could be good for an online chat prompt, IRL journaling, or something else that allows time for reflection.
5. Paper airplane / crane contest This one’s best for people who have some shared understanding already of each other, or will likely need one in the future, like a work training. Have people write something about themselves (again, make the prompt specific, like “draw your house” or “what was a creative halloween costume you did as a kid”). You can have people fold them into paper airplanes, fly them around the room, and each person takes one and guesses who wrote it. For a calmer version, string up paper cranes around the room.
6. Jenga with a prompt For my wedding and for Soapbox Seattle, we did giant Jenga where people could write directly on the blocks. For our wedding, we asked people to recommend date ideas. For Soapbox Seattle, we asked for sustainability tips. It’s always been wildly fun.

7. Rock Paper Scissors tournament or Ninja We did this every year with HUNDREDS of people for our Camp Galileo orientation, and I was excited to see Abbey teach it to Drew who brought it back to his session at GreenBiz24. It’s loud and gets the energy up immediately. It’s great to prime people for really interactive events, and maybe less great if you want everyone to feel comfortable and meet them where they’re at. I also loved Ninja for large groups who want to get movement going immediately.
8. Most Interesting Common Denominator Put people into groups of 5ish, either pre-selected or randomly selected. If you’re meeting IRL you can use colored hairties as wristbands or stickers from a secondhand craft store (yay, sustainability). If you’re meeting virtually, this is a great time to whip out the good old breakout room. Have people talk about the most interesting thing they have in common that’s probably not true for the other groups. For example, “we play soccer” might not cut it, especially if you’re hosting a gathering of athletes. If you’re pre-grouping people, you could pre-select the answer and have them try to figure out what it is—this is great when you know your guests but they don’t know each other.
9. Sing together Bar Karaoke is great for a reason. Civic Saturdays, which is meant to be a civic engagement and non-religious alternative to the community building provided by church, had song sheets for all of us, and it was a heartwarming and magical experience to connect neighbors. There’s no such thing as being a bad singer when you’re singing with a group!!
10. Flex imagination with past, present, and future conversation starters.

Conversation starter prompts are great when you have a clear vision of what they’re supposed to be used for. I love asking people about the past to build vulnerability and shared context. I love questions about the present because it can build connection in the here and now. Dreaming about the future and chatting about hypotheticals is awesome because it’s silly and boosts our sense of imagination and play.

Those are my icebreaker categories! I’ve included some specific conversation starters below, plus bonus…

I used to be a camp counselor for 6 years at Camp Galileo, so here’s a link to camp icebreakers. You never know when you’ll need them for adult settings.

Conversation-starting questions I love asking

Past

1. What is something you found interesting as a child that’s probably unique to you?
2. What are the best traits you learned or inherited from your family or schoolteachers?
3. What is the first thing you ever knew you were good at? Do you still use that skill today?
4. What were your friends like growing up? Are you still friends with each other?
5. Did you have any family or friendship traditions? Do you still do them?
6. What was a life-changing technology for you?
7. How do you think the beliefs of the adults in your life affected the adult you?
8. What did you think would be the best part of growing up? How does that hold up?
9. What did you imagine your life would be like?
10. When was the most courageous you’ve ever been?
11. What was something really simple that brought you a lot of joy as a kid?

Present

1. What’s something about you that we wouldn’t know from the internet?
2. What kind of stuff does your algorithm recommend to you?
3. What’s your most off-brand personality trait?
4. What’s your most serial killer personality trait?
5. What are the most annoying types of questions people ask you?
6. What are you curious about right now?
7. What is your favorite thing about yourself?
8. Why is it it important for you to be here today?
9. Who are the 5 most important people in your life?
10. If you could make ONE book, podcast, or movie required reading for everyone, what would it be?
11. What’s something about the state of society that deeply frustrates you? What are you doing about it?
12. What’s something really luxurious to your life that’s free or inexpensive?
13. How is your head? How is your heart?
14. Wanna swap contact info?

Future

1. What is the most unlikely, but theoretically possible good thing that could happen to you tomorrow?
2. If you could have a really minor superpower, what would it be? It can’t materially change your or someone else’s life. Something small like: knowing all the bathroom door codes. Or being able to make someone laugh right after they yawn.
3. If an alien came to earth for the first time, what would they observe about our planet and state of society?
4. What’s your plan for the apocalypse?
5. Imagine you wake up in the year 2200. What’s it like?
6. If you could get 1% better at something every day, what would it be?
7. What are you excited about for the future?
8. If you could invent something that makes your life 10x better, what would it be?
9. In a decade, you’re a world-renowned expert on something. It doesn’t have to be realistic. What is it?
10. I want to wish you good luck on something specific. What will it be?
11. Wanna hang out later?

If there is ONE thing I want us all to remember as we go about connecting people in this beautiful and messy world, it’s that listening to the people who are in your room matters the most. Icebreakers are great, but they’re a means to an end of creating meaningful belonging.

Let me know your favorites too, and I’ll update this post if I see any that I should include!

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