120 Questions to Ask Your Best Friend (and Turn Into a Game)

Turn the list into a game

1. 1Pick a question from any section below. The friend it is about answers honestly and keeps it secret for a second.
2. 2The other friend guesses what they said. In the WKYB app you both just tap your picks instead of saying them out loud.
3. 3Reveal both answers and score a point for every match. Swap who guesses and keep going until you have a match percentage.

Getting started

1. 1.How would you describe me to someone who has never met me?
2. 2.What was your first impression of me, honestly?
3. 3.What is your favorite thing about our friendship?
4. 4.What is something we have in common that surprised you?
5. 5.What is the best advice I have ever given you?
6. 6.What do you think is my biggest strength?
7. 7.When did you know we were going to be close friends?
8. 8.What is a small thing I do that you actually appreciate?
9. 9.What word would you use to describe me in one shot?
10. 10.What is your favorite memory of us from this past year?
11. 11.What do you think people get wrong about me?
12. 12.What is something you have never told me but always wanted to?
13. 13.How are we most alike?
14. 14.How are we most different?
15. 15.What is the first thing you noticed about me?
16. 16.What do you think I am secretly really good at?
17. 17.What is something I have helped you realize about yourself?

Funny

1. 1.What is the most unhinged thing you have ever seen me do?
2. 2.What is a song you cannot hear without thinking of me?
3. 3.What is the dumbest argument we have ever had?
4. 4.What is my most annoying habit, no holding back?
5. 5.What is the funniest thing I have ever said by accident?
6. 6.If our friendship was a reality show, what would it be called?
7. 7.What is the most embarrassing place we have ever been together?
8. 8.What is a weird food combo I love that grosses you out?
9. 9.What would the title of my autobiography be?
10. 10.What is the pettiest thing we have ever bonded over hating?
11. 11.If I were an animal, which one would I be and why?
12. 12.What is the worst outfit you have ever seen me wear?
13. 13.What inside joke of ours makes no sense to anyone else?
14. 14.What is the most chaotic group chat moment we have had?
15. 15.What is something I do that instantly makes you laugh?
16. 16.What is the dumbest dare we have ever done?
17. 17.If we got arrested together, what would it be for?
18. 18.What is my signature dance move?
19. 19.What is the weirdest thing we have ever Googled together?

Deep and meaningful

1. 1.What is something you are scared of that you have never said out loud?
2. 2.When was the last time you felt truly proud of yourself?
3. 3.What is a part of yourself you are still learning to accept?
4. 4.What does friendship mean to you now versus a few years ago?
5. 5.What is something you wish you could tell your younger self?
6. 6.What is a fear that has been holding you back lately?
7. 7.When do you feel the most understood?
8. 8.What is something you are grieving that no one knows about?
9. 9.What does your ideal version of your life look like in five years?
10. 10.What is a belief you have completely changed your mind about?
11. 11.What makes you feel safe with someone?
12. 12.What is the hardest thing you have ever had to forgive?
13. 13.What is something you need but find hard to ask for?
14. 14.When have I let you down, and did you ever tell me?
15. 15.What is a moment that genuinely changed you?
16. 16.What do you think you will care most about when you are old?
17. 17.What is something you are working on about yourself right now?
18. 18.What is the loneliest you have ever felt?
19. 19.What do you wish more people asked you about?

Memories and nostalgia

1. 1.What is the first time we ever hung out, do you remember it?
2. 2.What is the best trip or day out we have ever taken together?
3. 3.What is a phase we both went through that we will never live down?
4. 4.What old photo of us makes you cringe the hardest?
5. 5.What is a song that takes you straight back to a moment with us?
6. 6.What is the most we have ever laughed together?
7. 7.What is something we used to do that we should bring back?
8. 8.What is your favorite memory from when we first met?
9. 9.What is a tradition we accidentally started?
10. 10.What is the worst thing we have ever cooked or baked together?
11. 11.What is a time you were there for me that I might not even remember?
12. 12.What is the silliest thing we believed when we were younger?
13. 13.What is a place that just feels like ours?
14. 14.What is the longest we have ever gone without talking, and why?
15. 15.What is a moment with me you would relive if you could?
16. 16.What show or movie did we watch way too many times?
17. 17.What is the best gift we have ever given each other?

Hypotheticals and this or that

1. 1.Beach trip or mountain cabin for our dream getaway?
2. 2.If we opened a business together, what would it be?
3. 3.Night out or night in, what is our truest energy?
4. 4.If we won the lottery, what is the first thing we would do together?
5. 5.Coffee or cocktails for our catch-ups?
6. 6.If we could live in any city together, where would we move?
7. 7.Texting or calling, which one is more us?
8. 8.If we swapped lives for a week, who would struggle more?
9. 9.Road trip or flight for our next adventure?
10. 10.If we had to survive a zombie apocalypse, what is our plan?
11. 11.Spontaneous plans or everything scheduled in advance?
12. 12.If you could give me one superpower, which would you pick?
13. 13.Concert or festival for a perfect night?
14. 14.If we were roommates, what would we fight about first?
15. 15.Sweet or salty when we share a snack?
16. 16.If we could time travel together, which era are we visiting?
17. 17.Loud party or cozy dinner for my next birthday?
18. 18.If you could only keep one of my secrets, which one matters most?

Juicy and honest

1. 1.Who is someone you have always thought was not good for me?
2. 2.What is something I do in relationships that you wish I would stop?
3. 3.Have you ever had a crush you never told me about?
4. 4.What is a secret you have kept that you are dying to share?
5. 5.What is the most you have ever lied to me about, even something small?
6. 6.Who in our circle do you trust the least?
7. 7.What is something I have done that you secretly judged me for?
8. 8.What is the wildest thing that has happened to you that I do not know?
9. 9.Is there a topic you avoid bringing up around me, and what is it?
10. 10.What is the boldest text you have ever sent and regretted?
11. 11.Who is the one person you would never want to run into again?
12. 12.What is a rumor about you that was actually true?
13. 13.What is something you have done that you would never admit publicly?
14. 14.If you had to spill one of my secrets to save yourself, which goes?
15. 15.What is the most jealous you have ever been of me?
16. 16.Have you ever kept a friend drama from me on purpose?
17. 17.What is your most controversial opinion that you usually keep quiet?
18. 18.What is something you want from me but have been too shy to ask?

Future and dreams

1. 1.What is a dream you are scared to say out loud because it feels too big?
2. 2.Where do you hope we both are in ten years?
3. 3.What is one thing you want to do before you turn thirty, forty, or whatever is next?
4. 4.What does success actually mean to you?
5. 5.What is a place you swear you will visit one day?
6. 6.What kind of life do you want to build, in your own words?
7. 7.What is a goal you have that I could help you with?
8. 8.Do you want kids, and has that changed over time?
9. 9.What is a skill you have always wanted to learn but keep putting off?
10. 10.What would you do for work if money was not a factor?
11. 11.What is something you want our friendship to look like as we get older?
12. 12.What is a promise you want us to make for the future?
13. 13.What scares you most about getting older?
14. 14.What is one thing you hope never changes about us?
15. 15.If you could fast forward five years, what do you most want to see?
16. 16.What legacy do you want to leave behind?
17. 17.What is the next big risk you want to take?

Frequently asked questions

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