120 Interesting & Good Questions to Ask Friends, From BFFs to New Pals

These questions can spark meaningful conversations and deepen your friendships while adding fun and insight to your time together!

Juicy Questions to Ask Friends

What’s the craziest thing you’ve ever done for love?

Have you ever kept a big secret from someone?

What’s one rumor you’ve heard about yourself that wasn’t true?

Who was your first-ever crush, and do you still think about them?

If you had to kiss one person in this room, who would it be?

Have you ever done something super embarrassing in public?

If you could spy on one person’s life for a day, who would it be?

What’s the most rebellious thing you’ve done that your parents don’t know about?

Who’s the most famous person you’ve ever met or seen in person?

If you could redo one moment in your life, what would it be?

What’s a lie you’ve told that you’ve never admitted to until now?

Have you ever dated someone you knew was bad for you?

What’s your biggest regret when it comes to friendships?

Have you ever had a crush on someone you absolutely shouldn’t have?

If you could switch lives with one person for a day, who would it be?

Random Questions to Ask Friends

If you could live anywhere in the world, where would it be?

What’s your go-to karaoke song?

What’s the weirdest thing you’ve ever eaten?

Do you believe in ghosts or the supernatural?

What’s your dream job?

If you could time travel, would you go to the past or the future?

What’s the one movie you’ve watched more times than you can count?

What’s a skill you wish you could learn instantly?

If you won the lottery tomorrow, what’s the first thing you’d buy?

What’s your ultimate comfort food?

Do you believe in soulmates?

What’s the weirdest app on your phone right now?

If you had to pick one superpower, what would it be?

Have you ever walked out of a movie theater because the movie was bad?

What’s the most random compliment you’ve ever received?

Questions to Ask Your Best Friend

What’s one memory of us that you’ll never forget?

How would you describe our friendship in one word?

What’s the most valuable thing you’ve learned from me?

What’s something I do that always makes you laugh?

What’s your favorite inside joke that we share?

Have you ever lied to me about something important?

If you could plan the perfect day for us, what would it include?

What’s a song that reminds you of our friendship?

What’s the best advice I’ve ever given you?

If we could go on a trip anywhere in the world together, where would it be?

What’s one thing you’ve always wanted to tell me but never have?

How do you think we’ve both grown since we first met?

What’s something small about me that you really appreciate?

If we stopped talking for years, what’s the one thing you’d want me to remember about you?

Do you think we’ll still be close 20 years from now?

Deep Questions to Get to Know Them Better

What’s one experience in your life that changed you forever?

What motivates you to keep going when life gets hard?

If you could fix one mistake from your past, what would it be?

What’s your biggest fear in life?

How do you define happiness?

Who has been the most influential person in your life?

What’s one thing you wish more people understood about you?

What do you think your greatest strength is?

What’s a childhood memory that still brings you comfort?

How do you handle failure or rejection?

If you could change one thing about the world, what would it be?

What’s a belief or value that you hold above all else?

What do you think your purpose in life is?

What’s the most challenging decision you’ve ever had to make?

How do you want to be remembered by others?

Fun Questions to Ask Friends When You’re Bored

What’s the most ridiculous conspiracy theory you’ve ever heard?

If you could be any fictional character for a day, who would you be?

What’s your go-to guilty pleasure TV show?

If animals could talk, which one do you think would be the rudest?

What’s the weirdest habit you’ve picked up?

If you could switch voices with any celebrity, who would it be?

What’s the funniest thing you’ve ever overheard in public?

Would you rather fight one horse-sized duck or 100 duck-sized horses?

What’s the most useless fact you know?

If you had to eat one food for the rest of your life, what would it be?

What’s the worst fashion trend you’ve ever followed?

If you were a ghost, where would you haunt?

What’s the weirdest dream you’ve ever had?

What’s your go-to karaoke song after a few drinks?

If your life were a movie, what genre would it be?

Questions to Ask a New Friend

Where did you grow up?

What’s your favorite thing to do on weekends?

Do you have any hobbies you’re passionate about?

What’s your dream travel destination?

Do you prefer coffee or tea?

What’s your favorite childhood memory?

What’s one thing you’ve always wanted to try but haven’t yet?

Are you more of a morning person or a night owl?

Do you have a favorite movie or TV show?

What’s the best advice you’ve ever received?

What kind of music do you listen to?

What’s your favorite holiday and why?

Are you more of a city person or do you prefer the countryside?

What’s a skill you’d love to learn?

What do you usually do when you’re feeling stressed?

Hard Questions to Ask Friends

Have I ever hurt you without realizing it?

What’s something you’ve never forgiven someone for?

Do you think I’m a good friend? Why or why not?

What’s a personal challenge you’re currently facing?

Have you ever felt like I let you down?

What’s one secret you’ve never told anyone?

Do you feel like I truly understand you?

How do you handle conflict in friendships?

Is there something about me that you think I should work on?

What’s the hardest thing you’ve ever had to tell someone?

Do you think we’ve grown apart in any way?

Have you ever felt like I judged you unfairly?

What’s one thing you wish you could change about our friendship?

How do you deal with jealousy in friendships?

What’s the hardest goodbye you’ve ever had to say?

Personal Questions About Your Friendship

What’s your favorite memory of us together?

What do you think makes our friendship special?

How do you think we’ve both grown since we first met?

What’s one thing you value most about our friendship?

How do you feel we handle disagreements or conflicts?

What’s a funny habit or quirk you’ve noticed about me?

Do you think our friendship has changed over time? How?

What’s one thing you think we should do together more often?

If you had to describe our friendship in three words, what would they be?

How do you think we bring out the best in each other?

Is there anything about our friendship you wish were different?

What’s something I’ve done for you that meant a lot?

How do you feel about the way we communicate?

What’s a tradition or habit we share that you love?

How do you think our friendship has shaped who we are today?

FAQs: Good Questions to Ask Friends

Why is it important to ask meaningful questions to friends?

Asking meaningful questions helps deepen your connection, foster trust, and create more engaging conversations. It allows you to learn more about each other’s thoughts, feelings, and experiences, strengthening the bond you share.

How can I choose the right questions to ask my friends?

Select questions based on the context of your conversation and the depth of your relationship. For casual settings, opt for fun or lighthearted questions. For deeper connections, ask personal or thought-provoking questions that encourage sharing and reflection.

What types of questions are best for breaking the ice with new friends?

Questions that are open-ended, lighthearted, or centered around shared interests are ideal for breaking the ice. These help ease any initial awkwardness and create a comfortable environment for meaningful dialogue.

Can asking personal questions make friendships stronger?

Yes, when approached with sensitivity and respect, personal questions can build trust and understanding. They show genuine interest in your friend’s life and help foster emotional intimacy.

How can I make conversations with my friends more engaging?

Use a mix of lighthearted, fun, and thought-provoking questions. Actively listen to their responses, ask follow-up questions, and share your own perspectives to keep the dialogue dynamic and engaging.

What should I do if my friend seems uncomfortable answering a question?

Respect their boundaries and change the topic if needed. Not everyone feels comfortable sharing personal details, and it’s important to maintain a supportive and understanding environment.

Are there questions that can help resolve conflicts in friendships?

Yes, questions that encourage honest communication and understanding can help resolve conflicts. Ask open-ended questions about their feelings and perspective while avoiding accusations or assumptions.

What are some fun ways to use questions during group gatherings with friends?

You can turn questions into games, like truth-or-dare, icebreaker activities, or “would you rather” scenarios. This makes conversations interactive and entertaining while still encouraging meaningful interactions.

Can asking deep questions help with reconnecting after losing touch?

Absolutely. Thoughtful questions can help rebuild the connection by encouraging openness and reminding both parties of shared values, memories, and experiences.

What are the benefits of asking random questions to friends?

Random questions keep conversations fresh and unpredictable. They can spark laughter, curiosity, and even surprising revelations, making interactions more enjoyable and memorable.

How often should I ask my friends deep or personal questions?

It depends on your relationship and comfort level. Deep questions are best when the moment feels right, such as during quiet or reflective conversations, rather than forcing them in casual settings.

How can I ensure my questions encourage positivity?

Frame your questions in a way that focuses on uplifting topics, shared achievements, or lighthearted experiences. Avoid overly negative or confrontational topics unless they’re necessary for resolving a specific issue.

Are there any questions that are off-limits in friendships?

Questions that invade privacy, touch on sensitive issues without consent, or appear judgmental should be avoided. Always consider your friend’s comfort level and boundaries before diving into certain topics.

Can asking “hard questions” strengthen friendships?

Yes, hard questions can lead to meaningful conversations that deepen your bond. However, they should be asked with care and genuine intent, ensuring the other person feels safe and respected.

How can I encourage my friends to ask me questions as well?

Be open and engaging in your responses, and express interest in their curiosity about you. You can also lead by example, showing that asking and answering thoughtful questions is a two-way exchange.