Conversation Starter Questions

I made this list of questions to get beyond "what do you do" or small talk that doesn't go anywhere. I see someone I want to connect with, I know they have so much to share, but sometimes I have no idea how to start to dive in and really get to know them. These questions became a catalyst for playful and meaningful connections for me.

Most of the questions are collected - I didn't come up with most of them. But I have asked all these questions over the years and tailored this list to ones that seem to spark a real conversation. Open-ended questions are always the best and follow up with your curiosity. Be an active listener.  

Over the years I've heard stories of how these questions have been used.  Pull it out on a date, scroll and answer the question you stop on. Print them out, cut up each question and stick them in a jar at a party. Liven up a business meeting by having people introduce themselves and answer one question. Enjoy!

Openers

• What is the best thing that happened to you this week?
• What are you inspired by right now?
• What is the most interesting thing you’ve learned recently?
• Let’s find two things we have in common (besides where we are right now).
• What's been on your mind a lot recently?
• If you had to celebrate something this week, what would it be?
• How did you get to this very moment? (start as far back as you like)
• What community do you feel the strongest connection to?
• What is something you recently tried and loved?
• What did you fail at this week?
• What's one topic you could talk about for hours?
• What has surprised you recently?
• If you came with a warning label, what would it be?
• What are you absolutely determined to do? This week? This decade?
• High/Low/Learn - What was the high/low and what did you learn this from this day/week/event/experience?
• What’s something you are really into right now?
• What is something you have mastered?
• What would constitute a “perfect” day for you?
• What is your most prized possession?
• What moves your body?
• Which of your five senses do you treasure the most?
• What without fail always makes you laugh?
• What's the best thing you've ever purchased?
• What is the indulgence you spend the most money on?
• What is something everyone should experience at least once in their lifetime?
• What would cause you to immediately grab hand sanitizer?
• What is something that would surprise people about what it's like to be you?
• What's your favorite part of the weekdays?
• What are you famous for amongst your friends and family?
• What would be your ASL nickname (aka a one-handed gesture to represent you)?
• What are you interested in that most people haven't heard of or aren't into?
  
• What is your favorite guilty pleasure? 

Imaginative

• If you were to write a book/teach a class/give a TED talk, what would it be about?
• If you had a remote control for your life with one button, what would it be?
• If you could be reincarnated 5 times, who would you want to be reincarnated as?
• If there was a holiday in your honor, how would it be celebrated?
• You have reached your ‘ideal’ wealth, what does your life look like?
• How old would you be if you didn't know how old you are?
• If money was no object, what would you do with your life?
• If you could bring one fictional character to life, who would it be and why?
• Behind the hidden door is the childhood toy you seek in the environment you most fear. What is the toy and what the environment?
• If you could live anywhere, where would it be?
• What is something that doesn't exist yet but you think should have been invented by now?
• Everyone on Earth gets to wish for a superpower but you will only get yours if no one else wishes for the same power. What do you wish for?
• If you could spend a day in my body/head, what would you do?
• If an alien showed up right now, would you go with them?
• If you could get away with one crime, what would it be?
• If you had a billboard, what would it say?

POV

• What are some things us humans don't necessarily need that society makes us think we need?
• What childhood behavior do you wish was acceptable for adults?
• If you were to show around an out of towner, what would you highlight about where you live?
• What does this world need more of?
• What is obviously true but most people deny?
• What opinion of yours puts you in the minority?
• What is your relationship like with the universe?
• What is a sound/taste/smell/touch/sight you love?
• What is something important you take for granted?
• Where is the best place to see you in your prime?
• What do we do now that will be looked at as primitive and backwards in 100 years?
• What do you consider a wasted life?
• Ask for advice! Make the person feel like an expert, whatever the situation. Ex. What new tv show should I binge watch?
• What is something you do that society frowns upon?
• What's the oddest recurring thought that you have?

Achievements

• What does success look like to you?
• What gifts do you have to share with the world?
• What risk are you happy you took?
• What abilities do you have that you’re grateful for?
• What’s the best compliment/gift you’ve ever received or given?
• What is your greatest accomplishment?
• What award (real or fake) would you like to win and for what achievement?
• What’s one thing you’re deeply proud of but don’t normally share?
• What didn’t last forever, but was still worth the while?
• What are you working towards that you could use help on?
• What drives you to do better at something?

Characteristics

• If I were to grind you up and put you in a pill capsule and swallow you, what affects would you have on someone?
• What limits you from being yourself?
• What have you rebelled against in the past and what are you rebelling against now?
• How have your priorities changed over the last year?
• How would your friends describe you?
• What do you do that makes time fly/feel in flow? What is the core of that activity that you really enjoy?
• If you could wake up tomorrow having gained one quality or ability, what would it be?
• If your tombstone had three words on it, what would they be?
• Who are you when no one is looking?
• What are some things that you wish people knew about you?
• How do you express who you are?
• What do you make?
• What is the best way that you manage stress?
• What do most people think is true about you but isn't?
• What makes you feel good about yourself?
• What are your intentions for this week/event/year?
• What are you most grateful for, right now, in this moment?
• What is the #1 motivator in your life right now?
• What are three things you love about yourself?
• What is one of the nicest things anyone has ever done for you?
• What makes you feel better when you are bummed?
• What do you want your legacy to be?
• If this were a first date, what would you not want me to know about you?
• What is your favorite thing your body does for you?
• What is the best mistake you made?
• What makes your family unique?

Memories

• What's the most impactful drug experience you've had?
• Have you ever had a now or never moment?
• Where were you exactly a year ago?
• What was your personality like as a child?
• What is the best surprised you ever pulled off?
• What is your most treasured memory?
• Which age was the best year of your life? Why?
• What would you go back and tell your teenage self?
• Whom have you lost touch with but still wonder about?
• What is one life lesson that you learned from a mentor that changed your perspective on life?
• What did your parents teach you that you had to unlearn?
• What can you do today that you couldn’t do a year ago?
• What’s something you said you would never do, but have since done?
• What is the last time you did something evil?
• What big lesson could someone learn from your life?
• What three events define your life?

Deep

• What is so important to you that you would stand in front of a bus to defend it?
• What is the next chapter of your life?
• What is the title of the current chapter of your life?
• What values are strongest in your family?

• What conversation should you be having in your life that you aren't, and who with?

• What is something deep inside you that needs to come out and be shared with the world?
• What would put you out of your comfort zone right now?
• What is your purpose in life?
• What statistic for your life would you most like to see?
• When did you first realize you were an adult?
• When was a time you discovered an edge?
• If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
• What is the best and worst case scenario for your current challenge?
• What are your core wounds from childhood?
• What is a lie you keep telling yourself?
• How are you like (or not like) your mom and dad?
• What was an inflection point in your life where you thought you were going down one path but ended up somewhere unexpected?
• What is an object that has had a big impact on your life?
• How do you seek validation?
• What is pulling at your heart?
• If you really knew me, you would know…

The Dark Side

• What challenge do you want to overcome?
• When have you felt the most alone?
• What is something you have been putting off?
• What is something you don’t understand but are too embarrassed to ask about?
• When was the last time you cried? Why?
• What is a pattern you need to release?
• What, if anything, do you think is missing from your life?
• What is your biggest fear?
• What would you do if you weren’t afraid?
• What are your pet peeves?
• How do you react when you don't get what you want?
• What scares or excites you the most about the future?
• Are you holding onto something that you need to let go of? What’s stopping you?
• What kinds of issues do you have with your friends?
• What is the scariest thing that's ever happened to you?
• Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
• What do you live in denial about?
• If you knew you were going to die tomorrow, would you have any regrets?
• If you could eliminate one limitation/weakness from your life (besides money) what would it be?
• What ideas or thoughts scare you the most?
• What do you spend too much time doing?
• Do you think other people can be trusted?
• If you have one day/month/year to live, how would you spend it?
• What is something you probably should do, but will never do? Why not?

Relationships

• What is your relationship with flirting? What is your flirting style?
• Who is an important person in your life besides a family member or romantic partner?
• Which person has the greatest influence over your life?
• What are the qualities you look for in a friend?
• Why did you break up with your last partner?
• What is one way you helped another person this week?
• Whose life do you believe you’ve had the biggest impact on?
• What is the best thing about your dad and/or mom?
• What’s the biggest mistake you’ve ever made in a romantic relationship?
• What is something uncommon that you find attractive?
• What is the biggest romantic gesture you’ve ever given or received?
• How do you show love to others?
• What are the pivotal moments in our/your relationship?
• Of the following ways, how do you express love to another person: touch, verbally, time spent together, acts of kindness, or gifts?
• How do you show yourself that you love yourself?