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A ton conversations help in deepening those friendships. But if you’re not skilled at making up conversation starters, don’t fret.

From funny ice breakers that will catch everybody off guard, to deep questions that can possibly open up a can of emotions, here is a massive list of questions for friends, which you can pick and pluck from.

60 Fool-proof Questions for Friends to Get to Know Them Better

How well do you know your friends? Make your conversations count by asking meaningful questions.

Question about relationships

With these questions, you’ll get your friends talking about their past and current relationships.

  • How old were you when you had your first kiss?
  • Who was the last person who broke your heart?
  • What is your biggest turn off when it comes to a potential partner?
  • Do you like to be left alone or comforted after a fight?
  • What is your must-have attitude in a partner?
  • Would you go for smarts over looks?
  • How do you connect best with others?
  • What are your top 3 deal breakers?
  • Do you regret any of your relationship choices?
  • What 5 things make relationships successful?

Question about you

Make your friends talk about themselves. It is the easiest way to really, truly get to know their deepest thoughts, values, and personality.

  • What do you love most about yourself?
  • Is there a person you inspire to be?
  • Do you ever regret doing something?
  • What makes you the happiest? the saddest?
  • Do you get stage fright?
  • What chores do you secretly love doing?
  • Do you have a family tradition you vow to continue?
  • What hobbies are on your perpetual to-do list?
  • Are you an expert on something?
  • What’s your favorite smell?
  • Are you comfortable eating out alone?
  • Do you have a culinary specialty?
  • Do you have a collection nobody knows about?
  • Do you have a hidden tattoo?
  • Are you able to voice out your opinions freely?
  • Where is your favorite place in the world?
  • Do you have a dream car?
  • What is your earliest memory?
  • What is your greatest fear?
  • What do you miss being a kid?

Fun questions

Use these fun questions if you need to break some ice before asking more serious questions.

  • Which gaming app do you use the most?
  • Do you have a favorite superhero?
  • What conspiracy theories do you believe in?
  • Do you have a movie villain crush?
  • What is the weirdest thing you watched online?
  • What websites do you visit daily?
  • What’s the dumbest thing you’ve ever agreed to do as a dare?
  • Can you survive without social media? If you can only keep one, which platform would you choose?
  • Do you believe in the paranormal?
  • If a genie grants you 3 wishes, what would they be?

Would you rather questions

“Would you rather” questions are light and easy to ask, but they actually show your friend’s likes and dislikes.

  • Drink coffee or tea?
  • Eat cookies or brownies?
  • Watch Netflix or go to the movies?
  • Have a grand wedding or get married in city hall (with your honeymoon traveling around the world)?
  • Read a book or listen to music?
  • Go on a diet or start a workout routine?
  • Wear rubber shoes or slippers?
  • Write your thoughts or speak out?
  • Skip breakfast or dinner?
  • Wear your raggedy shirt or buy a new one?
  • Dance by yourself or with other people?
  • Browse Pinterest or Twitter?
  • Drink beer or cocktails?
  • Go on a hike or swim?
  • Death by shark or zombie?

Interesting questions

Want to learn how your friend’s brain works? These questions will give you some clue.

  • Do you have a weird recurring dream?
  • If you could learn a language fluently, what would you choose?
  • What day will you never forget?
  • How close are you with your coworkers?
  • If you can get a dinosaur or dragon as a pet, which would you pick?
  • Have I done something to you that you’ll never forget?
  • What’s the last thing you did for the first time?
  • If you are given the power to erase a holiday, what would it be?
  • Have you ticked anything from your bucket list?
  • What’s the most impressive event you’ve attended?

Deep questions: When you should take out the big guns

It’s tricky to just blurt out questions about a friend’s hopes and dreams, beliefs and opinions. Sometimes, the timing isn’t right. Or your friend may not be ready to open up to you just yet.

So when should you start asking serious and deep questions? Are there any unspoken rules to this? There’s 3:

1. Nothing is off limits

You can talk about anything, from the grossest food you’ve ever eaten, to the most embarrassing things you’ve done. If you and your friend already bonded over boogers or what you’d do in a zombie apocalypse, then you can probably dig deep and talk about serious conversations as well.

2. You can cry, laugh, or burst into a hissy fit in front of each other

If you or your friend just let each other’s emotions run loose without judgment, it’s also the perfect time to get to know one another better.

3. You’ve kept each other’s secrets for a long time

There’s a reason why some people consider hanging out with their friends as free therapy.

Sometimes, serious questions could open up closed wounds, or bring back trauma. Other times, it could highlight a person’s trust issues.

If you know in your heart that you can be trusted with any secret your friend shares with you, then your friend would probably feel safe telling you things he/she keeps so dearly.

15 serious questions to bring your friendship to the next level

If you answered yes to all 3 rules above, then you’re ready to take out the big guns and get deep. You can start off with these serious questions:

  1. What’s your proudest moment in life?
  2. If you can quit your job today and do anything, what would it be?
  3. Are there specific moments in your childhood that molded who you are today?
  4. What’s your biggest regret?
  5. How do you see yourself in 10 years?
  6. What do you value most in friendships?
  7. Do you have a hunch of what would be your future cause of death?
  8. Has life been hard on you?
  9. What keeps you at night?
  10. If you can choose your last meal, what would it be?
  11. Do you believe in miracles?
  12. Do you have a weakness you’re trying to overcome?
  13. Would you prefer a burial or a cremation?
  14. What 3 things are you most thankful for today?
  15. Are you happy with your life right now?

✍️  August 29, 2020

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List of great questions to ask your friends

Conversation Starters

Whether you’re at a party talking to someone you’ve just met or spent time with friends you haven’t seen in awhile, coming up with a good conversation starter that isn’t just boring small talk can be a struggle. When you begin a discussion with someone, you want it to be interesting, insightful, and entertaining.

Conversation Starters