Questions for Icebreakers | 20 Ultimate Get to Know You Questions
I’m letting you in on my gold mine of questions I like to ask when I am in a group or with someone I want to get to know better. Before trying these out on just anyone, you have to really know who you are with and if they are going to be willing to answer your questions.
Also, if you aren’t prepared to really listen to the person’s answers, then don’t ask! These are for when you genuinely want a group to connect with each other or just go deeper than surface level conversation. Remember, these questions aren’t just a box you can check off – they are meant to get the conversation flowing into something more. It’s up to you to keep asking more questions or to discuss everyone’s answers with more depth.
The best part about these questions is that it shows you how someone thinks. Maybe they answer in a way you hadn’t thought about before. They might have no idea what to answer because they hadn’t thought about it before. Either way, their answers will show you a lot about how they view the world and themselves.
Let’s get into it:
1. What is your dream?
I ask this question, and I follow it up with: regardless of money, status, talent, or time, what is your dream? If you could do anything, be anything, or achieve anything, what would it be? It can be realistic or far out there.
Whenever they answer, if it’s something they could really accomplish or do, I always ask them why they aren’t doing that. If it’s something that’s far out there and would more than likely not happen, I still try to follow up and ask if there’s something that they really could see themselves doing and still try to keep the conversation open that way.
This question is my all-time favorite question, because it tells you so much about a person. It helps you take a glimpse into the person’s mind and what is most important to them. It shows you how that person looks at the world and what success or hope looks like for them. This question is the ultimate way to see how someone thinks about the world and about themself.
2) If you had 3 wishes, what would they be for?
This is a classic question, but again, it shows you what someone truly wants or it shows their personality. Did they give a classic answer that everyone gives? Did they give a thoughtful answer? Or, are they being a jokester and deflecting?
I’m the person that really doesn’t know what I want, so while I give somewhat classic answers, it always makes me question my own wants and desires out of life. Why am I unsure of what I want? Will I ever get what I want?
3) What are your 3 passions? What are your 3 anti-passions?
This will help you see what someone loves. Notice if their list has to do with hobbies, or social issues, or qualities. There are so many answers, and I love that.
On the other hand, anti-passions show you what someone dislikes. I call them anti-passions because I hate to ask what someone hates, because that doesn’t quite do the question justice. Anti-passions are more about what someone is strongly against. The answers I always get are hilarious, and I would love to hear about what answers you get on this question!
4) What is your least and favorite quality about yourself?
This one gets a little personal, but it’s always interesting. Does the person talk about their physical qualities, or do they talk about their characteristics? It’s helpful to see what people value as a part of themselves and also what their insecurities may be. This helps me see what I need to be wary of in conversation with someone if I might hit a nerve.
It also shows me what I might not have seen in a person if I didn’t know them so well before. Their favorite quality about themself might be something I didn’t know about them, and it’s helpful to see how that person views themself. Also, it’s good to be able to verbalize something we like about ourselves! It shows humility to be able to acknowledge not just our weaknesses, but also our strengths.
5) If you could go anywhere right now, where would you go?
While it’s my dream to travel literally everywhere in the world, some people just simply want to go to a beach or to their family’s cabin, or somewhere they can relax. The answers always vary on this one, and I love that. It shows you what people are craving at that moment and what their idea of traveling, relaxation, or vacation is for them.
I will always say someplace extravagant, because I don’t always get to do that. For some people who are constantly busy and on the go, they might just say their favorite beach or just their home. The most important part is that you don’t judge what the other person says.
Sometimes I forget that a lot of people don’t necessarily spend all their free time looking up destinations or places to explore. I wonder why they don’t want to go to an extremely foreign destination. This helps remind me that everyone is different, and I have no right to judge what someone finds valuable.
6) When was the last time you felt sad and why?
Another tough question, but this one is great for a one-on-one conversation or also in a small group of friends just looking to really talk. While it’s hard to talk about, it is important to see that everyone has struggles and what I might not think about as being difficult could be something really tough for someone else. This question also helps you see what someone is currently struggling with or it could show you that the person is truly happy. They might not have been sad in a long time, or they were sad yesterday. Either way, you are able to see that other people are going through things even when it might be easier to gloss over those topics.
7) What were the best 3 days you ever had?
I love hearing about people’s top 3 days. Sometimes they are jam-packed full of amazing things, and sometimes it’s just about days that had a big moment. Either way, this gives me a glimpse into someone’s life and what they see as being the most defining or joyful for them. I love hearing about those happy moments. It also helps the other person get to relive and remember those amazing days! It’s the best of both worlds.
On the other hand, if I see those top 3 days as being small moments, I get to take a step back from my life and look at what truly matters to me. Why does it have to be the biggest life-altering days that were my favorite? Why can’t those simple days of being with people I love and spending time doing things I love be my favorite days? I get to see both perspectives, and it’s amazing to reflect on those ideas.
8) What’s a bad personal habit you have?
Again with the vulnerability, I know. But it’s important! It’s important to be able to speak openly and honestly about stuff that we struggle with. I know I have bad habits, and when I ignore them or try to hide them, it makes them harder to overcome. By actually saying what they are out loud, I now have people to hold me accountable. I also have a way of admitting it to myself.
The good thing is that I know this is the case for so many people. I think we try to only put our best foot forward most of the time. In reality, we need to not feed into the narrative of giving our highlight reel to people. That’s why with this question, I’m quick to answer first so that they know it’s okay to be honest and to speak about that struggle.
9) What is one quality, characteristic, or virtue you want to work on?
Maybe some people might think this is a dumb question, but I love it. It goes along with admitting your weaknesses. If you don’t want to ask about weaknesses and instead just keep it positive, this is your question. This helps keep a positive spin, because you’re not just saying that you don’t like something about yourself.
You could be really terrible at that quality or you could just want to be better at it because it’s important to you. In any scenario, it’s so interesting to see what people find as being important characteristics in themselves.
10) If you could tell your younger self something, what would you say?
This question speaks not only to past regrets or mistakes, it speaks to what someone knows now. It shows what that person has learned about life and what they wish they knew earlier. I love hearing about lessons other people have learned, because a lot of times it’s something I never thought about. Or, it’s something I needed to hear.
It could also give me new perspective on what someone else didn’t know that helps me open my mind to how I view other people. In any case, it shows you someone’s growth.
11) What’s your biggest fear?
Obviously, I’m going for a deeper fear instead of just spiders or heights. But, if someone does answer with a classic answer, I always ask more questions about that. What about that thing do you fear? Usually, there’s something deeper going on there.
If someone answers with being afraid of death or being imperfect or not being in control, I like to really talk about that. Again, this shows an insecurity, and it helps me know how to best talk to that person and what could be triggering. We don’t have to be brave all the time.
12) What do your hands say about you?
I know this is probably the strangest question on this list, but I love it. I love it, because it’s so out there. People’s hands show their struggles, what they work on, what they value, and what they struggle with. My hands will show that I am anxious because I bite my nails all the time. Some people’s hands have perfectly polished nails, and some have calluses from manual labor. It’s a strange question, but people’s hands tell a story.
13) Who is the person you want to be, and does it compare to who you are now?
While this has a little bit to do with your goals and your dreams, this is different. This question specifically is asking about where a person is on their journey. Are they actively working towards the person they want to be? Or, are they unsure of how to get there? Have they already pinpointed the type of person they want to be?
On the other hand, are they happy with who they are? Maybe it’s about how they got to be the person they wanted to be instead of where they still need to go. There’s so much to be inferred from this question.
14) Do you feel like you present a specific version of yourself to certain people or that you are the same with everyone?
I know this one is a bit specific, and some people may not relate to this at all. But, what I’ve found is that often, people change who they are based on who they are with. Why do they do this? What aspects do they hide? Are they not comfortable with certain parts of themselves?
This question shows how people view themselves and also what they like most about themselves. It also could show that people are scared to show parts of themselves to some people.
15) If you could change one thing about your life right now, what would you change?
Maybe some people have something they actively are wishing for or working towards. They could also have everything they need or want. Or, they could be exactly in the right place at the right time. People often have something they can answer, and this shows you what they want at that point in their life. It could be something broad or something specific. I love the variety of answers I always get.
This question is meant to bring out hope – hope for the future and hope of all that life can bring.
16) What are three things you love about your life?
It’s always a good idea to bring out gratefulness in conversations. This questions helps me remember to reflect more on what I love about my life instead of all the things I want to change. I love seeing what people value in their lives and also everything good that has happened for them. I love getting to know what I should be more grateful for.
Also, I love knowing how to make sure that I’m feeding into a person’s life in a way that’s valuable to them. This is so important, because this person is practically telling you how you can add value to their lives in meaningful way.
17) How have you changed in the past year?
As you can see, I’m all about growth. I love seeing where a person has come from and where they are going. When I can, I love to encourage people to grow more. This question is perfect for helping someone reflect on their life and what has changed for them in just one year. It’s always so crazy to think back to where I was just last year and how much I have grown.
Hearing about other people and where they have come from in just one year is amazing. Maybe they haven’t really changed much, and they are content. Maybe they haven’t really changed much, but they want to and don’t know how. There’s so many answers. Some people have made dramatic life changes, while some people are making small steps to get there. Sometimes I need that encouragement that change and growth is possible.
18) What is a talent you wish you had?
There are so many talents I wish I had. Sometimes I hate that about myself – when I can’t learn something or I’m just not good at something. But, a lot of times, I am actually impressed when somebody is so talented at something I can’t do. It’s fun to see what people might see as a talent they wish they had.
Sometimes, people say they want to be talented at something I already think they are good at. Other times, people say they wish they want a talent that is rare. They even might say they want to be talented at personality traits instead of a traditional talent. You just never know with this question, but it definitely tells you something if you take the time to look.
19) What’s the secret to happiness?
It’s always good to get free advice. Maybe you will take the advice and maybe you can filter it out if it doesn’t suit you. Either way, I love knowing how people view happiness. Some people think it’s simple, and some people can’t put words to it.
Asking about the secret to happiness is like asking someone to come up with a short description of everything they’ve learned in life. In short, it sums up what they are about as a person.
20) Are you happy?
Everyone wants to be happy, but are they? Some people will spout off a quick “yes!” After thinking about it, they realize maybe the answer should have been no. A lot of times people want to give off the appearance that they are happy when maybe they aren’t. Other times, people aren’t sure. They haven’t thought about it.
Asking someone if they’re happy is interesting, because happiness is an emotion. It is fleeting, and it can come and go. This being said, a lot of people consider it the ultimate destination. So, asking if someone is happy is intensely personal, but it’s a good moment of reflection for all parties involved.
Again, these questions are meant to be asked to fill space. They are personal and raw and real. They help everyone think and reflect, and it’s important to remember to continue the conversation. We can’t just ask someone a question if we aren’t really ready to listen.
