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

_Category: Best Friends · 125 questions · from Who Knows You Best? (https://whoknowsyou.best)_

The best questions to ask your best friend go past surface chit-chat and pull out real stories, hot takes, and memories. Use them as conversation starters, or make a game of it: one friend answers privately, the other guesses, and you score a point for every match to see how well you really know each other.

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

## Getting started
- How would you describe me to someone who has never met me?
- What was your first impression of me, honestly?
- What is your favorite thing about our friendship?
- What is something we have in common that surprised you?
- What is the best advice I have ever given you?
- What do you think is my biggest strength?
- When did you know we were going to be close friends?
- What is a small thing I do that you actually appreciate?
- What word would you use to describe me in one shot?
- What is your favorite memory of us from this past year?
- What do you think people get wrong about me?
- What is something you have never told me but always wanted to?
- How are we most alike?
- How are we most different?
- What is the first thing you noticed about me?
- What do you think I am secretly really good at?
- What is something I have helped you realize about yourself?

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

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

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

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

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

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

## FAQ
**What are good questions to ask your best friend?**

The best ones mix light and deep: funny memories, honest hot takes, hypotheticals, and a few meaningful questions about fears and dreams. Variety keeps the conversation flowing and helps you learn something new instead of repeating the usual small talk.

**How do you turn these into a game?**

Pick a question, have one friend answer it privately, and let the other guess what they said. Score a point for every match. The WKYB app does this automatically with hidden answers and a final match percentage.

**What questions actually deepen a friendship?**

Questions about fears, proud moments, what makes someone feel understood, and how the friendship has changed tend to open people up. They invite real stories instead of one-word answers, which is where real connection happens.

**Are these questions good for new friends too?**

Yes. Start with the getting-started and funny sections to keep things easy and low pressure, then move into deeper or juicier ones once you both feel comfortable. There is no rush to get personal.

**How many questions should you ask in one sitting?**

Around fifteen to twenty is a sweet spot. It is enough to go beyond surface level without it feeling like an interview. If you are playing it as a guessing game, agree on a number first so scoring stays fair.

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Play it with a friend or partner in the Who Knows You Best? app (iOS): https://apps.apple.com/us/app/who-knows-you-best-bff-quiz/id6758728112