60+ Questions to Deepen Friendships: Fun, Personal and Mindblowing

Get to know anybody and forge meaningful friendships online with these mindblowing, fun questions to ask friends.

Think you know everything about your BFF? With these exciting questions to ask friends, we’re giving you more tools to learn a thing or two.

Asking questions — millions of them — helps us better understand others, expand our perspectives and deepen interpersonal bonds. So why have we stopped diving head-first into new people's minds when meeting online?

Not all questions are created equal. In this article, we'll explore different types of inquests and how they help build meaningful relationships or overcome challenges in online conversation. Keep these at hand when initiating a one-to-one video chat on Azar to see how far you and your online friends can go!

What Hinders Us From Asking Questions?

Often, what stops us from asking questions emerges as a social pattern from our subconscious depths: We may not realize we're doing it — or the opportunities potentially missed as a result. Delving into online friends’ ideas exposes us to fresh learning and fortifies interpersonal bonds. Here are a few reasons why we may forget:

• Desire to Impress: Making a good impression with our perspectives and stories can feel so important that we forget to ask a person about themselves.
• Nonchalance or Distraction: When distraction takes over, we might lose focus or expect to be bored by a response. If this crops up, tune into your curiosity — there are infinite ways new pals may surprise you.
• Overconfidence: If we believe we already know an answer, it might feel less important to ask. The key to a great discussion is openness to learn and challenge our beliefs in friendly chats.
• Fear of Being Judged: Hands up if you've felt like you've asked a dumb question before. Spoiler alert: We all have — and we're still here to tell the tale. Showing an interest in someone else with silly questions outweighs a lack of enthusiasm, so go ahead and ask.

Bringing awareness to how you take interest in new friends online is the first step to strengthening relationships. Below, you'll find a few nifty ways queries can guide you through challenges and usher even deeper bonds.

How To Handle Questions in Cooperative Conversations

Cooperative discourse is when two people vocally collaborate toward a common goal. There's not much space for error here, right? But you know what they say about too much of a good thing.

Two primary challenges can emerge even in excellent conversations. Here's what they are and how to handle them:

Encourage Authenticity When You're Asking Questions

Particularly when things are flowing smoothly with a new comrade, we can tend to brush over any bad news or shy away from conflicting views to retain good vibes. While it's often done with the best intentions, only keeping things in the light can introduce shades of inauthenticity to a connection. This concept fringes around what psychologists call ‘Masking.’ Keep it real (and positive) with these tips:

• Ask Open-Ended Questions: These remove the conversational focus from negative points or conflicting opinions. Open questions give the other person space to answer honestly on a foundation free from bias or judgment.
• Be Respectful: You may not agree on everything, and staying receptive to alternative views encourages your convo partner to express themselves liberally, reinforcing the bond.
• Show Empathy: Opening up to someone new about a less-than-ideal scenario can be difficult. Meet vulnerability with empathy and watch how the authenticity between you grows.

Retain Balance When You're Answering Questions

Interesting conversations can feel like a verbal happy hour where words are on free flow. And sometimes we forget to keep our chats inspiring and cooperative or take the stage a little too long. Here's how to keep things on track:

• Try not to get too caught up speaking only about yourself. Aim for a balance and leave space for your new pal to plug in some insights.
• Ask plenty of questions.
• Use energy, humor and storytelling to keep the discussion engaging.
• Dodge tough inquiries by answering with a new question or a joke.

Navigating Questions in Uncomfortable Conversations

We'd usually define a ‘closed’ conversation as when you or your chat partner is reluctant to open up and share. Questions help open dialogue when someone's not feeling talkative. However, be mindful that personal history, current vibes or the stage of trust development between you can make anyone reluctant to reveal personal information — and that's totally valid.

During a 'closed' convo, one (or both) of you may feel uneasy shouting your life story and worldly secrets from the treetops. But a few methods are available to help get the tea on your new friend's celebrity crush or protect your peace — if needed. Here's how:

Get Talking With Questions

The goal here is to help your friend open up, right? Try following this approach to help them relax into casual dialogue:

1. Ask small questions that merit little responses.
2. Pitch detailed follow-up probes, easing them into light expansions gradually.
3. Once they're comfortable, ask slightly more open queries.
4. If you sense the other person is uncomfortable, throw a pivot question in and steer the convo into a different terrain.

Avoiding Uncomfortable Questions

There may come times when you're feeling interrogated and are uncomfortable expanding. Use these tactics to respond gracefully:

• Think in advance about any information you'd rather not discuss in the conversation to avoid answering impulsively. It's impossible to predict all the questions someone may ask, but having awareness around any subjects on the ‘Nope’ list will give you a good starting point.
• Maneuver by responding to a similar question you're comfortable answering.
• Reflect by asking a different question in return.
• Consider how or when to open up and be vulnerable with someone, as this can build trust.
• Have a backup response prepared, such as “I'd prefer not to answer that,” or, “That subject is not on the cards today.”

The first thing to remember is that you're always in control of the information you share with someone else and the topics you discuss. Our second pointer is it's perfectly natural to feel a little social anxiety or freeze up in conversation now and then.

If you want to build up some practice, boost confidence and level up your convo game, connect with and meet new people in one-to-one video chats online and participate in real conversations in Azar — an easy-to-use video chat app. Here are some types of questions you might ask your online friends:

Types of Questions to Ask: An Overview

Especially when chatting digitally, questions help pivot the conversation, keeping the vibes engaging and fun. Here are some of the query types you'll likely run into and how they function in convos:

Introductory Questions

Example: What's your favorite color?

This is basically small talk to garner elementary information about a person and their interests. They help us get to know our chat partner and lead to deeper, more meaningful expression.

Mirror Questions

Example: My favorite color is turquoise, what's yours?

Mirror questions may bat back and forth between two people to show reciprocal interest or to deflect talking too much about oneself. They're helpful at first but tend to become more sparse as the conversation naturally progresses.

Follow-up Questions

Example: I like yellow. Do you have any special memories associated with turquoise?

Want to show your chat partner you're listening and interested? Use follow-up questions. These explore the other person's response to extract more information or perspective on a subject.

Pivot Questions

Example: Turquoise reminds me of the ocean. Have you ever seen an octopus in real life?

A pivot question will steer the discussion in a nuanced direction or change the focus entirely. These can be used tactfully to avoid uncomfortable subjects or reinvigorate the energy of your interaction. Note that if they're used too randomly and often, your convo partner may feel unheard.

Open-Ended Questions

Example: No, I haven't. Why do you think an octopus has eight arms?

Open ended questions invite perspective. They have no right or wrong answer. If a person feels backed into a corner with too much interrogation, an open probe can expand the dialogue to include insights, ideas or stories.

As you read through the list of questions to ask friends below, consider how to create a natural flow in video chats by weaving your own ideas into the conversation.

20 Friendly and Fun Questions For Light-Hearted Chats

Lighthearted, funny questions have a way of invoking our inner child, opening the stage for sharing personal interests and being as goofy as you want. Often, these topics lead into a related story helping you to understand one another better.

If you're stuck for conversation starters, these make great icebreaker questions as well:

1. If you could have dinner with any fictional character, who would it be and why?
2. What's the most embarrassing thing you've ever done to impress someone?
3. If you were a superhero, what would your superpower and superhero name be?
4. What's the weirdest food combination you've tried and actually liked?
5. What's your favorite holiday tradition?
6. If you could switch lives with any celebrity for a day, who would it be and what would you do?
7. What's the funniest or weirdest dream you've ever had?
8. Where is your favorite place to be during a storm?
9. If you could instantly become an expert in anything, what would it be?
10. What's the most ridiculous fact that you know?
11. What's your earliest or favorite memory from childhood?
12. What's the weirdest thing that happened to you in middle school?
13. If you had to sing karaoke right now, what song would you choose?
14. What's your guilty pleasure TV show or movie?
15. How many photos do you think you're in the background of?
16. What's the best gift someone could buy you for pure enjoyment?
17. If you were a cat, what would be your favorite way to get attention?
18. What is your favorite story from childhood and why?
19. What's the funniest way your name has been misspelled?
20. What was your dream job as a kid?

20 Philosophical and Personal Questions to Strengthen Friendships

Get to know how your friend works under the hood with these deep questions. They require reflection and vulnerability, so be careful not to layer them on too quickly. Others may feel uncomfortable speaking about personal matters, so approach these with care and respect. If you sense the person is not at ease, perhaps revert back to some more lighthearted questions.

However, sharing profound personal insights in an online chat where you can feel safer opening up has the potential to give you something to muse over and steadily build trust.

1. What is a moment or event in your life that significantly shaped who you are today?
2. What do you think is the purpose of life or your life in particular?
3. How do you define true happiness and do you think you've achieved it?
4. What is your biggest fear and how do you confront it?
5. If you could change one thing about the world, what would it be and why?
6. What is a personal belief or value that you think is critical to who you are?
7. How do you cope with difficult times or situations in your life?
8. What role do you think love plays in your life and how has it impacted you? 
9. How do you want to be remembered after you're gone?
10. What do you consider to be your greatest achievement or proudest moment?
11. What is the biggest challenge you face right now (and is there anything I can do to help)?
12. What trait do you see in yourself that you admire in other people?
13. If you wrote an autobiography, how would you divide your life into chapters?
14. If growth comes from mistakes, why are we afraid to make them?
15. If you lost everything that you consider important now, what would keep you going?
16. If anything is possible, how do you know what's worth trying?
17. What's something you learned as an adult by reflecting on your younger self?
18. How many places do you think you've visited for the last time?
19. Which family member do you feel closest to?
20. What does an ideal life look like to you?

20 Mindblowing and Funny Questions For Powerful Conversation

Interesting questions like these don't have a right or wrong answer. They're designed to get your mind reeling, challenge beliefs and make you laugh. The following list is a great segue into deeper conversation and more meaningful relationships.

1. What is freedom? Is it doing what you want or having the option to?
2. If you didn't know how old you were, how old would you be?
3. Is it ever too late?
4. At what age do we stop being young, and when do we start being old?
5. If everything is possible, could it be possible for something to be impossible?
6. What defines art?
7. What color would you say a mirror is?
8. Where do our thoughts go when we lose track of them?
9. Do you think fish can feel sadness?
10. Why do we value logic and reason highly when there is so much they can't explain?
11. Is reality confined to our sense of perception?
12. Do good and evil exist outside of the human construction of them?
13. Is it harder to let go of a problem, or solve a problem?
14. What does your pet think about when you're not around?
15. If the best things in life are free, why do we buy stuff?
16. If you never learned to speak a language, how would thoughts appear in your mind?
17. Is the answer to this question no?
18. Would it be better never to forget or never remember?
19. If black absorbs light and white reflects it, what does silver do?
20. If you were abducted by aliens, what kind of experience would you hope for?

Ready To Use These Questions?

Questions help make one-to-one video chats fluid and expansive. You can use them to build perspective, make new pals and foster powerful social connections.

It's one thing to make digital allies; it's another to build profound relationships through intentional online communication. With Azar, you can open dialogue with like-minded people from across the globe instantly by initiating a one-on-one video chat.

Try out these questions to ask friends and boost your confidence in a light and breezy environment like Azar. Start Chatting now!