👋 Check-in
•
💌 All Topics
How well are you taking care of yourself lately?
Level 1
🎲 Random & Fun
•
💌 All Topics
Who here is is most likely to eat cat food?
Level 1
👋 Check-in
•
💌 All Topics
Where you currently facing uncertainty or unknown, and how are you navigating it?
Level 2
👋 Check-in
•
💌 All Topics
Is there a quote or saying you call to mind often, intentionally or unintentionally?
Level 2
💼 Work & Career
•
💌 All Topics
When you think of the legacy you want to leave, does your current job contribute to that vision?
Level 3
🤔 Self Reflection
•
💌 All Topics
Are you waiting on someone or something to progress in an aspect of your life?
Level 3
🌎 Worldview & Life
•
💌 All Topics
What's one thing you would change that's commonly taught to children today?
Level 3
💜 Relationships
•
💌 All Topics
What's something you wish you knew earlier about being a good partner?
Level 3
🎲 Random & Fun
•
💌 All Topics
Who here is is most likely to join the secret service?
Level 1
🎲 Random & Fun
•
💌 All Topics
You're gifted 24 hours where you and your pet(s) are suddenly able to talk to each other. What would you want to tell them, and how would you want to spend your time with them?
Level 2
💼 Work & Career
•
💌 All Topics
What's your least favorite part of your job and why?
Level 1
💜 Relationships
•
💌 All Topics
What's a recent moment in which you're proud that you spoke up?
Level 1
💼 Work & Career
•
💌 All Topics
What tools or apps do you find indispensable for your work?
Level 1
🌎 Worldview & Life
•
💌 All Topics
If you could have witnessed one event from your family history, what would it be?
Level 3
🎲 Random & Fun
•
💌 All Topics
What fictional character would you most like to have as a mentor?
Level 2
🎲 Random & Fun
•
💌 All Topics
What's a great name for a pet but a terrible name for a human?
Level 1
🌎 Worldview & Life
•
💌 All Topics
What do you believe is the most significant factor in shaping one's destiny, and how much control does one have over it?
Level 1
🧊 Icebreakers
•
💌 All Topics
What's the most valuable lesson you've learned from a culture different from your own?
Level 3
💜 Relationships
•
💌 All Topics
What have you previously tolerated that you no longer allow in your life?
Level 3
👋 Check-in
•
💌 All Topics
How's your family doing?
Level 1
💜 Relationships
•
💌 All Topics
Which relationships have become more meaningful to you as of late?
Level 1
🤔 Self Reflection
•
💌 All Topics
What's one thing about you that hasn't changed in the last 10 years?
Level 2
👋 Check-in
•
💌 All Topics
What have you been dreaming of eating lately?
Level 1
👋 Check-in
•
💌 All Topics
What do you have up in your browser tabs right now?
Level 1
🎲 Random & Fun
•
💌 All Topics
If you could learn one secret from anyone, who would it be and what would it pertain to?
Level 2
🤔 Self Reflection
•
💌 All Topics
What's your biggest dream?
Level 1
🤔 Self Reflection
•
💌 All Topics
What trait do you admire in others but don't possess yourself?
Level 3
🤔 Self Reflection
•
💌 All Topics
When do you feel most like yourself?
Level 1
👋 Check-in
•
💌 All Topics
What quality are you currently cultivating in yourself?
Level 2
💜 Relationships
•
💌 All Topics
Is there anyone who intimidates you? Why do you think this is?
Level 2
🎲 Random & Fun
•
💌 All Topics
If you were perpetually surrounded by one aroma (asides your own, natural scent) which you and everyone around you could smell, what would it be?
Level 2
🌎 Worldview & Life
•
💌 All Topics
In what ways do you think hardship can contribute to personal growth?
Level 2
💼 Work & Career
•
💌 All Topics
What's a funny or embarrassing moment you’ve had at work?
Level 1
🌎 Worldview & Life
•
💌 All Topics
What is the single most critical issue you would want your child to be passionate about addressing in their lifetime?
Level 3
💼 Work & Career
•
💌 All Topics
On a scale of 1 to 10, how valued do you feel at work?
Level 1
👋 Check-in
•
💌 All Topics
What's an interesting conversation you recently had?
Level 1
🤔 Self Reflection
•
💌 All Topics
What activity absorbs you completely and makes you lose track of time?
Level 1
🎲 Random & Fun
•
💌 All Topics
If you were a teacher, what would you teach and what ages would your students be?
Level 2
🎲 Random & Fun
•
💌 All Topics
A surprise package arrives at your doorstep — it's from everyone here! What's inside?
Level 2
👋 Check-in
•
💌 All Topics
Think of one of your big, lofty goals. What small step could you take today towards achieving it?
Level 2
🌎 Worldview & Life
•
💌 All Topics
Think of your biggest regret. If you could go back in time and make a decision to keep it from happening, would you?
Level 3
👋 Check-in
•
💌 All Topics
How did you spend your most recent weekend?
Level 1
💜 Relationships
•
💌 All Topics
Are there any relationships in your life that feel imbalanced? What would it look like to restore balance?
Level 2
💜 Relationships
•
💌 All Topics
What's your ideal first date?
Level 2
👋 Check-in
•
💌 All Topics
What aspects of life are you loving most right now?
Level 2
💜 Relationships
•
💌 All Topics
What's a recent moment in which you feel you represented yourself authentically?
Level 1
🌎 Worldview & Life
•
💌 All Topics
Is there anything you think your generation does better than the next generation?
Level 1
🤔 Self Reflection
•
💌 All Topics
Are you settling for less than what you are worth? If so, why?
Level 2
🤔 Self Reflection
•
💌 All Topics
How would you summarize your last 12 months in one sentence?
Level 1
🎲 Random & Fun
•
💌 All Topics
If you could change one thing about yourself physically, what would you change?
Level 3
🎲 Random & Fun
•
💌 All Topics
What scientific or technological advance blows your mind?
Level 1
🎲 Random & Fun
•
💌 All Topics
If you had to give a TED Talk without any preparation, what topic would you choose?
Level 3
🎲 Random & Fun
•
💌 All Topics
Which superpower would you pick to subtly make your everyday life easier?
Level 3
🎲 Random & Fun
•
💌 All Topics
What's the best compliment you've ever received?
Level 3
💜 Relationships
•
💌 All Topics
Before having a conversation with someone, do you ever rehearse what you are going to say? Why
Level 1
💜 Relationships
•
💌 All Topics
To what degree do you modify your behavior based on who you're with? Do you think this is good or bad?
Level 1
🎲 Random & Fun
•
💌 All Topics
What's one thing you miss the most growing up as a kid?
Level 1
💼 Work & Career
•
💌 All Topics
What's a common myth about your profession that you can debunk?
Level 1
👋 Check-in
•
💌 All Topics
How is your current health, fitness, or wellness routine going?
Level 1
🤔 Self Reflection
•
💌 All Topics
What was your "rock bottom"? How did it happen, and how did you get out of it?
Level 1
👋 Check-in
•
💌 All Topics
What can you be kinder towards yourself for right now?
Level 2
🌎 Worldview & Life
•
💌 All Topics
You can impart one understanding about human relationships to your child. What insight do you choose to share?
Level 3
🎲 Random & Fun
•
💌 All Topics
Who here is most likely to leave their inheritance to a ferret that only has a 3-year lifespan?
Level 1
🧊 Icebreakers
•
💌 All Topics
What's something you've achieved that you never thought possible for yourself?
Level 3
🎲 Random & Fun
•
💌 All Topics
You can stop time for 24 hours. What do you do with this opportunity?
Level 3
💼 Work & Career
•
💌 All Topics
What profession would you be in if you had known about it earlier?
Level 3
🧊 Icebreakers
•
💌 All Topics
What's your earliest memory?
Level 2
🧊 Icebreakers
•
💌 All Topics
If you could travel anywhere in the world right now, where would you go and why?
Level 1
🌎 Worldview & Life
•
💌 All Topics
What do you think is the best place or way to meet a signifcant other?
Level 1
🧊 Icebreakers
•
💌 All Topics
What are people surprised to learn you're really good at?
Level 2
🧊 Icebreakers
•
💌 All Topics
If you had to choose a theme song for your life, what would it be?
Level 2
🤔 Self Reflection
•
💌 All Topics
What stopped you from following, or encouraged you to follow, your childhood passion?
Level 1
🤔 Self Reflection
•
💌 All Topics
What bad habits would you like to get rid of? What steps do you need to take to make that happen?
Level 1
🎲 Random & Fun
•
💌 All Topics
What's an ethical dilemma that keeps you up at night?
Level 3
👋 Check-in
•
💌 All Topics
What do you wish people would ask you more about right now?
Level 2
👋 Check-in
•
💌 All Topics
What is one thing you didn’t do so well recently?
Level 1
🎲 Random & Fun
•
💌 All Topics
What is something you love, that everyone else hates?
Level 3
🤔 Self Reflection
•
💌 All Topics
What is an irrational fear you have?
Level 2
🧊 Icebreakers
•
💌 All Topics
Where were you born?
Level 1
💼 Work & Career
•
💌 All Topics
If you could try out any other profession for a day, what would it be?
Level 1
🤔 Self Reflection
•
💌 All Topics
When was the last time you cried and why?
Level 2
🎲 Random & Fun
•
💌 All Topics
What are some bad things you did as a teenager?
Level 1
🧊 Icebreakers
•
💌 All Topics
What's a memorable lesson you've learned from a mistake you've made?
Level 3
🌎 Worldview & Life
•
💌 All Topics
Who in your life do feel is receptive to receiving feedback?
Level 3
💜 Relationships
•
💌 All Topics
Complete this sentence: "I wish I had someone with whom I could share ... "
Level 1
🌎 Worldview & Life
•
💌 All Topics
How has your definition of happiness changed as you've gotten older?
Level 3
💜 Relationships
•
💌 All Topics
What advice would you give about maintaining long-lasting relationships?
Level 3
🤔 Self Reflection
•
💌 All Topics
What is the quality you admire the most in the person you dislike the most?
Level 3
🧊 Icebreakers
•
💌 All Topics
Which best describes you? An introvert or an extrovert?
Level 1
💼 Work & Career
•
💌 All Topics
Are you currently mentoring anyone, or being mentored? How is that going?
Level 2
💜 Relationships
•
💌 All Topics
How do you resolve conflict with the closest people in your life?
Level 3
🧊 Icebreakers
•
💌 All Topics
What do you think is the most significant impact individuals can make in the world today?
Level 3
🎲 Random & Fun
•
💌 All Topics
Who here is most likely to dedicate their life trying to go to another planet?
Level 1
🎲 Random & Fun
•
💌 All Topics
You're given a sidekick with any superpower of your choosing. What's their name, and what's their power?
Level 3
🤔 Self Reflection
•
💌 All Topics
What lesson have you had to learn again and again?
Level 2
🌎 Worldview & Life
•
💌 All Topics
What is the most trivial thing about which you have a strong opinion?
Level 2
💜 Relationships
•
💌 All Topics
How well do you receive feedback?
Level 2
💼 Work & Career
•
💌 All Topics
Have any failures played a significant role in your your career development?
Level 2
💼 Work & Career
•
💌 All Topics
How do you describe your current job to someone who's not in your industry?
Level 1
👋 Check-in
•
💌 All Topics
What has surprised you recently?
Level 1

Connection Questions

by Letterloop 💌

600+ questions to stay in touch, grow closer together, and discover things you never knew with the people in your life.

Start your own Letterloop →

Topics

Reset filters
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.