Good conversation starters with your best friend

Good Question... 45+ Deep Conversation Starters with Friends

There’s a reason deep, meaningful talks can have lasting effects on your relationships. We asked two experts how to go about starting those kinds of conversations.

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You may think you know someone, but do you, really?

Whether you’ve known them a day or a decade, there’s something about a profound conversation that can help you see people in a whole new light and, hopefully, strengthen your bond.

If you feel intimidated about jumping into the deep end of dialogue, you’re not alone. So we rounded up 5 examples and 45 questions to help you get started.

Deep connections are based on curiosity and vulnerability, and an imperfect, real exploration, says Jackie Tassiello, a therapist in the greater New York City area.

“Relationships need nurturance; they’re not static,” she says. “Through intentional conversation starters, we’re metaphorically watering the plant of our relationship. We’re providing the care and energy that goes into growth.”

“The safety of deep relationships is the foundation for so many healing benefits,” she adds. “Some [2017] research shows that when we feel completely safe with someone, our nervous system relaxes in a way that invites healing and growth.”

What types of questions are best to get to know someone deeply?

You may have seen the viral “36 questions to fall in love” experiment on YouTube.

The original research behind this comes from a series of experiments by psychologist Arthur Aron in the 1990s. He was able to measure how intimacy forms between two strangers in just 45 minutes with a series of deeper and deeper questions.

It works for people in existing relationships, too.

In his book “Eight Dates: Essential Conversations for a Lifetime of Love,” Dr. John Gottman indicates that 4 decades of research shows that in healthy relationships, people make time to be curious and get to know one another.

Kimberly Panganiban, a licensed marriage and family therapist in San Diego, California says, “In order to do this, try to ask open-ended questions. These could be past-, present-, or future-oriented.”

“The goal is to strike a conversation in which you both learn new things about one another and, therefore, feel more connected. Questions that generate discussion about emotions can bring the deepest connection,” adds Panganiban.

Types of questions

Some helpful types of questions may include:

Open-ended: What’s one movie that made you tear up and why?
Past: What’s the most memorable dream you’ve ever had?
Present: What’s the most important quality to you in a friend, right now?
Future: What’s one quality you hope to change about yourself in the future?
Needs-oriented: How can I best support your needs right now?

As humans, we are all wired for connection. It’s necessary for our survival and it supports our mental health in many ways, says Panganiban.

“Connection helps us to feel secure in life and about ourselves, which allows us to engage more with the world,” she explains.

“When our basic need of attachment is met, it leaves us open to pursuing other interests, goals, and adventures. We feel a sense of comfort and safety, knowing we have people that we can count on and that love us,” she adds.

A list of questions at the ready can help take some of the pressure off.

(In)frequently asked questions

What’s a quality you still want to have at age 90?
What book has influenced you the most?
What’s your #1 goal right now?
What’s your quirkiest habit?
What do you like the most about being “you”?
What’s one fear you want to master?
Who’s your role model, dead or alive?
What was your favorite novel as a kid?
What’s a quote that inspires you?
What’s your greatest achievement so far?
What subject did you look forward to in school?
Are your priorities different from what they were 10 years ago?
Has your character been shaped by anyone?
What’s your favorite memory of helping a stranger?
What’s the earliest thing you remember as a child?
Have you had any recurring nightmares?
What’s a recent lesson your parents/caregivers taught you?
If you had a time machine, what year would you travel to?
If you had a free hour, how would you spend it?
In all of history, who would you spend an afternoon with?
If you could travel anywhere in the world for dinner, where would it be?
What animal would you want to be for a day, and why?
What would be the topic of your New York Times bestselling book?
If you had paints right now, how would you fill a blank canvas?
How do you define success?
What is the cause of cruel behavior in the world?
How can you tell when you have chemistry with someone?
In all of human history, what’s the most important event?
Why are we here on this planet?
What’s one truth you’ve learned about being a human?
When you think about the future, what makes you nervous?
What would help you feel the most relaxed right now?

What’s the biggest challenge you’ve overcome?
What’s a time when you failed, and what did it teach you?
When you feel self-doubt, how do you push through it?
Can you recall the last time something made you cry?
What’s the biggest trigger for your stress?
What happened on the greatest day of your life?
How do you think all of Earth’s different religions came to be?
Do you believe in miracles?
Do you believe in prayer and, if so, how do you do it?
What makes you feel lonely?
Do you believe that humans have a soul that lives on?
What’s a secret about you that you haven’t told anyone?
What makes you feel the most alive?

Being a skilled conversationalist takes practice. A good set of communication skills can help you show interest in what your someone is saying.

When you ask someone a question, for example, you may find it helpful to employ a few active listening techniques, such as:

nodding
asking for more details
maintaining eye contact
repeating back what they said
responding with encouragers, including “hmm” and “interesting”
giving someone your full attention — that means not looking at your phone

There’s an art to ending a deep conversation. Without some finesse, things could feel awkward or incomplete.

The first step is picking the right moment. It’s a good idea to wrap things up when:

there’s a natural lull
you notice a sense of “completion”
your conversation partner looks bored or uncomfortable
a person, or device, interrupts the flow
there are body language cues that show they’re ready to go
you’d like to reflect

When the opportunity arrives, you can thank your conversation partner and suggest a lighter follow-up activity. For example, this could sound like:

“Thank you for opening up to me. I really enjoyed this conversation. I hope we can have more of these in the future. Would you like to split the bill and take a quick walk in the sun, before I have to head back to work?”

What if a conversation takes a downturn?

In the event of a downturn, try to use this as an opportunity to keep improving your connection by offering compassion, validation, or in some cases, an apology, says Tassiello.

“Downturns are a part of the deal when we’re in deep with someone,” she says. “Instead of fearing that aspect, bring yourself into the present moment and ask how you can be supportive around the topic next time, or what the person needs.”

Meaningful conversations can help deepen your interpersonal connections, which in turn, can help improve your overall health and well-being.

When you’re done with the 45 questions above, you can keep the conversation flowing with Gottman’s Card Decks, which are available in an app form on your device, says Panganiban.

You may also find it helpful to sift through “The Complete Book of Questions: 1001 Conversation Starters for Any Occasion” by Garry Poole.

201 Good Questions to Ask Friends, From BFFs to New Pals

Think you know everything about your BFFs? You probably know a lot, but you can always go deeper. Sometimes dedicating a night to a Q&A for friends is not only beneficial for your relationships but also, it can be hilarious. There are plenty of interesting questions to ask friends, even if you’ve known them most of your life.

And no matter how many years you’ve known them, being a best friend means continually finding new ways to show care and invest in your bestie. Asking questions that expand your understanding of what makes them tick — from the experiences that have shaped them to their hopes for the future — is a great way to do that. We’ve rounded up the best questions, ranging from silly to serious, that are sure to bring out all the feels and spark a stronger bond between you.

But of course, your BFF didn’t become your ride or die overnight. Knowing what kinds of questions to ask your friend group at large, including new friends, will help you cultivate closeness with everyone in your circle. That’s why we’ve also included questions for friends and questions to ask to get to know someone, so you can deepen your bond with pals who aren’t a BFF — yet.

So, grab your bestie for a best friend questions video date, or pull up this list of 201 fun questions to ask friends the next time you’re hanging with your group. You’ll be surprised by how much there is to learn about people, no matter how far into the friendship you are!

In this article:

Juicy questions to ask friends

Random questions to ask friends

Questions to ask your best friend

Fun questions to ask friends

Questions to ask a new friend

Juicy questions to ask friends

When it comes to friendship questions, these are the ones that will dig the deepest. Prompts like this are best brought up late at night during a sleepover, right before you all hit snoozetown.

1. What’s the weirdest thing you’ve done in public?

2. What’s an embarrassing thing you’ve done and never told anyone about?

3. What’s the most bizarre text you’ve ever received?

4. What’s the cringiest thing you’ve ever put up on social media?

5. What do you feel the most guilty about?

6. Who do you wish you could reconnect with?

7. How much does your personality change when you’re around different people?

8. What stresses you out the most?

9. When do you feel the most alone?

10. Have you ever been in love?

11. Do you believe in love at first sight?

12. What’s the biggest lesson your last relationship taught you?

13. What’s the nicest thing someone has done for you?

14. If someone wrote a book about you, what would it be called?

15. What’s one thing you would change about yourself?

16. Do you believe in having one best friend?

17. How do you define beauty?

18. Who is someone you wish you could apologize to?

19. What was the last turning point in your life?

20. What thing keeps you going on hard days?

21. Who do you feel the safest around?

22. What’s your favorite childhood memory?

23. What’s the biggest leap of faith you’ve taken?

24. What do you think is the most annoying quality a person can have?

25. Who do you think shouldn’t be a celebrity?

Random questions to ask friends

Sometimes the situation just calls for a random question or two. Head right this way when you’re looking to laugh a little.

1. Have you ever had a crush on a cartoon character?

2. Would you ever open a business?

3. What’s the worst holiday in your opinion?

4. What are you putting off right now?

5. Did you build forts when you were a kid? What did they look like?

6. What do you think the best prank of all time is?

7. If you got to design a new instrument, what would you create and what would it sound like?

8. Is there anything you’d wait in line for a week to do, see, or get?

9. If flowers could talk, what do you think they would sound like?

10. If you could choose only one condiment to eat for the rest of your life, which would you choose?

11. If you could be any household item, which would you choose?

12. If you were a ghost, how would you haunt people?

13. What bodily function do you wish would just go away?

14. If you had to eat an entire barrel of one single thing, what would you choose?

15. If you could shoot anything from a cannon, what would you pick?

16. Do you have a favorite family tradition?

17. Describe your dream house.

18. What’s your favorite cheesy joke?

19. If you could name your brain, what would you name it?

20. What subject would you take a crash course in?

21. What’s your favorite form of transportation?

22. If you could only dress in one color for the rest of your life, which would you choose?

23. How gullible do you consider yourself?

24. What do you think you’ll be doing exactly 10 years from this moment?

25. What’s the spiciest food you’ve ever eaten?

Questions to ask your best friend

Reserve these for the people you know best. Some things are meant for the friends you’ve been through everything with.

Most Popular

1. What embarrasses you the most?

2. Who do you look up to the most, and what qualities do you love about that person?

3. What’s your biggest fear?

4. What’s your love language?

5. How do you like to be comforted when you’re sad or upset?

6. What’s your all-time favorite memory?

7. Who was the last person to make you cry and why?

8. Where do you hope to be five years from now? Ten? Fifteen?

9. When have you felt the most proud?

10. When have you felt the most challenged?

11. Have you ever been bullied?

12. Do you have any regrets? If so, what are they?

13. Which celeb would you want as your other BFF and why?

14. Out of all your family members, who are you closest to?

15. What do you do when no one else is around?

16. What’s one thing most people don’t know about you?

17. What do you think happens when we die?

18. Do you want to have kids one day? How many?

19. What's the best present you ever received? Who gave it to you and why was it so special?

20. What's the worst you've ever been physically hurt?

21. What's your earliest childhood memory?

22. If you could change one thing about yourself, what would it be?

23. Do you believe in soulmates?

24. When you can't sleep, what keeps you up at night?

25. What has your hardest goodbye in life been so far?

26. What's the last lie you told?

27. What's the best compliment you've ever received?

28. What do you consider the ultimate comfort food?

29. What do you consider your best physical feature?

30. What are the top three things that stress you out?

31. What are the top three ways you deal with stress?

32. When was the last time you were jealous and why?

33. If you could only have three things on your life bucket list, what would they be?

34. What’s the worst decision you’ve ever made?

35. What’s something you’d consider unforgivable?

36. If you choose to get married one day, what would your dream proposal scenario be?

37. What’s the most loved you’ve ever felt?

38. If you could create a theme park, what would it look like?

39. When’s the last time you felt inspired to create something?

40. Have you ever experienced a “friendship breakup”? What did it teach you?

41. Who was your first friend, and are they still in your life?

42. Would you ever consider being in a long-distance relationship?

43. What do you think the best way to resolve conflict is?

44. How did your parents meet?

45. Do you feel that you have a healthy relationship with social media?

46. Who’s been your favorite teacher?

47. What are your favorite childrens’ names?

48. What do you think you’ll be like in old age?

49. Is there a time when I made you feel particularly well supported?

Most Popular

50. How can I be a better friend to you?

51. What does friendship mean to you?

Fun questions to ask friends

Fill the silence with these goofy queries.

1. Would you rather be an expert at one thing, or pretty good at many things?

2. What’s your favorite thing you own and why?

3. Have you ever had your fortune told?

4. Would you rather order in or eat out?

5. What was the first movie you remember seeing in theaters?

6. What’s your favorite podcast?

7. What’s been your most questionable haircut and/or fashion moment?

8. If money was no object, what would you buy?

9. What did you dream about last night?

10. When was the moment in your life you laughed the hardest?

11. What do you do when no one else is around?

12. Where do you want to travel the most?

13. If you could only eat one thing for the rest of your life, what would it be?

14. What book has impacted you the most?

15. Do you believe in monogamy?

16. What’s your favorite commercial?

17. What are the qualities that attract you most in a love interest?

18. You just won $10,000 — what are you going to do with the money?

19. What's the luckiest thing that's ever happened to you?

20. What's your favorite way to exercise?

21. Do you like roller coasters?

22. What is your most hated chore and why?

23. What's your favorite holiday and why?

24. What’s the worst date you’ve ever been on?

25. If you were going to get some ink, what would you choose and why?

26. If you had three wishes, what would you wish for?

27. If you had to choose only one, would you pick a dog or a cat?

28. Do you believe in aliens?

29. If you were President, what's the first thing you would work to change in this country?

Most Popular

30. If you had to live in another time period, what would you choose?

31. Who was your very first crush?

32. What foreign language(s) would you want to master and why?

33. What's your all-time favorite dessert?

34. Do you believe in ghosts?

35. What’s your survival plan during a zombie apocalypse?

36. If you were an animal, what would you be?

37. If you had to create an alter ego for yourself, who would it be and what would you name them?

38. What’s your No. 1 karaoke song?

39. Have you ever been on a blind date?

40. What was your AIM screen name, or your first email address?

41. What’s your favorite piece of random trivia?

42. What was your first concert?

43. Which decade, in your opinion, had the best fashion trends?

44. If a song played every time you entered a room, what would it be?

45. What’s your skincare routine?

46. Did you ever go to summer camp?

47. When’s the last time you got to really experience nature?

48. Do you feel that you’re young at heart, or an old soul?

49. What does your name mean, and why was it given to you?

50. What’s an unexpected movie that makes you cry?

Questions to ask a new friend

When you’re first getting to know someone, stick to the important (and high-level) questions. After all, they may spark some deeper conversation.

1. What are your pronouns?

2. What would be your perfect day? Plan it out from waking up to bedtime.

3. What’s your zodiac sign?

4. What’s your Enneagram type?

5. On vacation, are you the relax-by-the-pool type or a get-up-and-go adventurer?

6. Do you consider yourself religious or spiritual?

7. What college major are you thinking of choosing and why?

8. If you could only listen to one singer or band for the rest of your life, who would you choose?

Most Popular

9. What's your go-to dish when you have to make dinner?

10. Are you a superstitious person?

11. What’s your favorite board game to play?

12. Who’s the best movie villain?

13. Who’s your favorite follow on TikTok? On Instagram?

14. Did you have an imaginary friend growing up?

15. If you had to describe yourself in only three words, what would you choose? What words do you think your friends would choose to describe you?

16. Do you have any phobias?

17. What are your top three biggest pet peeves?

18. What's your favorite color and what's your least favorite color?

19. What would your dream vacay consist of?

20. Are you competitive?

21. What’s a tough experience that you learned and grew from?

22. What’s your relationship with your parents like?

23. Do you most often follow your heart or your head?

24. What’s the most unexpected or unusual thing on your bucket list?

25. What was your last romantic relationship like?

26. What’s a value you’re unwilling to compromise on?

27. What's your absolute dream job?

28. If you could have a superpower, what would you choose?

29. What TV show do you turn on when you just want to zone out and feel better?

30. What was the last movie you watched in a theater?

31. If you could time travel, where would you go?

32. What do you usually have for breakfast?

33. What's your favorite plant or flower?

34. What’s your favorite season and why?

35. Who always makes you laugh?

36. What do you think your best quality is?

37. What is your definition of success?

38. What’s your most-watched movie?

39. Do you have any hidden talents?

40. What’s the best thing you’ve dressed up as for Halloween?

41. Would you rather live by the ocean or in the mountains?

42. What’s the longest trip you’ve taken?

43. Are you a right brain or left brain person?

44. What is your most-used emoji?

45. What’s a bad habit you’re trying to break?

46. What’s the scariest movie you’ve ever seen?

47. Are you a morning person or a night owl?

48. Do you like to recharge alone or around other people?

49. What’s the best museum you’ve ever been to?

50. When can we hang out again?

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13 Tips for Starting a Conversation

How good do you think you are as a conversationalist? Have you ever had awkward pauses in a conversation? A few tips described in this article will help you become a better conversationalist, and awkward pauses will be a thing of the past. Being a good conversationalist is just a combination of different methods of communication. Body language, a few tricks and you will be able to easily carry on a conversation with any people.

Start with a question

Do you want the person to remember you? Ask him an interesting question and listen carefully. This will give you the opportunity to make friends.

Get someone else's opinion

For example:

Could you recommend me a good cocktail?
Do you know the city well? Can you recommend me a good restaurant?
Where did you buy this phone/accessory/clothes?
What do you think of this party?

Applying an economic concept to a conversation

Imagine that your conversation is a bank. If you have a lot of investments, then things are going well. If loans are more than investments, then something should be changed. Transferring this metaphor to communication, we get this.

Imagine that your conversation starts with a zero balance and do everything to increase it!

Copying body language

The practice of copying body language can be very helpful. Is your interlocutor cross-legged? Cross yours. Put your hands on the table? Do the same. Everything is very simple. Time is also very important. Wait for the moment:

When the interlocutor tells something interesting
When you are interested
When the interlocutor is proud of something

And then copy it. The person will assume that you empathize with him and it will be great if this is true.

How to talk about yourself without being terribly boring

You can be an incredibly charismatic and interesting person. But, people are just not interested in hearing about others, no matter how wonderful you are. If you continue to follow our economic concept, then you must make an emotional investment. Make the interlocutor experience emotions and he will be very interested in talking with you.

Change the depth of the conversation

You know the proverb: small minds discuss people, average minds discuss events, and great minds discuss ideas? Use it. Start small and play a prank on someone, then get the other person's opinion on an event, and then move on to ideas related to that event. For example:

Intro: Hello, how was your day?

Event: Are you planning something with Katya for Valentine's Day?

Idea: I saw an article on the internet about how we have perverted Valentine's Day from its traditional meaning.

Ask the other person to be interesting

Everyone is interesting in their own way, but few people really open up. So give them a chance to open up and they will only think of you. Here is a simple example:

Tell me something interesting about yourself.

This is a great conversation starter that will make you seem more attentive and at the same time give you the opportunity to learn something really interesting about the person.

How to ask people what they do

How do you spend your time when not. ..?

Instead of a blank at the end, there should be something you know about the person. Here are a few examples:

How do you spend your time when you're not writing your exciting blog?

How do you spend your time when you are not on Facebook*?

How do you spend your time when you don't go to the gym?

Be a good listener

If you were to ask me for one piece of advice on how to be a good conversationalist, I would stop there. This is the most important part. Listen to the person. Be genuinely interested in what he is talking about. Lead the interviewer's story with your questions. Be interested in him and he will be interested in you in return.

Pace of conversation

In general, a fast pace of conversation is a sign of nervousness and excitement, while a moderate pace is a sign of confidence. Therefore, try to speak at a moderate pace, but if your interlocutor speaks at a fast pace, copy it and speak the same way.

Correctly change the topic of conversation

This has happened to everyone: you are discussing something with your acquaintance, but then a third person bursts into your conversation and turns the whole conversation in his direction. It's terribly annoying. But, only if you're doing it wrong. You must make an emotional investment at the end of your monologue. This will divert attention and you won't look like an idiot by changing the subject. Example:

Chris: My son is a very good football player.

Me: Cool! You once talked about where he trained. My son recently earned a black belt in Karate and is leaving for Korea on a student exchange program. After all, your son trained in Korea? Can you give me some tips?

In this dialogue, the emotional investment was a compliment to Chris and his son. I changed the topic of conversation to the one I needed, doing it right.

Give the Right Compliments

Compliments are a very powerful tool when used correctly. The correct way to use compliments is to make them about what the person is proud of. For example:

If the person is in good shape and obviously spends a lot of time in the gym, compliment their figure.
If the person is successful in their career, compliment their creativity, business acumen, or intelligence.

Don't compliment people's qualities if they haven't made it on their own. Don't tell a beautiful girl that she is beautiful. She already knows it.

Unite friends

If you are at a party or social event, you are unlikely to stand in one place. Most likely, you will go from one group of acquaintances to another. If you see people you know in different groups, don't be afraid to invite them to talk together. Do it with a joke and without tension. And then your friends will remember you as a very friendly person.

*Activities of Meta Platforms Inc. and its social networks Facebook and Instagram are prohibited in the territory of the Russian Federation.

How to start a conversation with friends or strangers: 5 proven ways

January 23, 2013 Relationship

These simple tips will help you build contacts and stop being shy at a crowded party or gala reception.

Not everyone likes small talk about nothing. In fact, such conversations perform a very useful function: they help to defuse the situation, get out of an awkward situation or start communication in an unfamiliar company, as well as unobtrusively start a conversation and get to know a new interlocutor better.

To be honest, I used to think that the ability to unobtrusively start a conversation was an exceptionally innate talent. With these people, after a couple of minutes you feel like you are talking with an old good friend. And I personally know such people - there are not so many of them in my environment.

In addition to them, there are comrades who just as easily start conversations with strangers, but after a minute they become like representatives of a Canadian company trying to sell you another set of knives, dishes or a vacuum cleaner. There is a huge difference between the first and second. How to understand that you are too carried away, and how to start a conversation correctly? Here are five simple tips from Celes, author of the Personal Excellence blog.

1. Ask a question

The easiest and most standard way to start a new conversation, many use it.

"What do you do?"

This is a great conversation starter in countries with a culture of work, such as Singapore or Hong Kong. People from there are used to identifying themselves with their occupation. If you know that this person loves his job and devotes a lot of time to it, feel free to ask. You will get a long enough and detailed answer, so that the conversation will not end after a short phrase and an awkward pause. Also, the method is well suited for talking at various conferences, seminars and business events. After that, you can ask a huge number of more working questions: “how long has he been in this business and has been working at this company?”, “Does he like this job?”, “What prompted him to join this company?” and so on. Questions about clients, business trips, careers, and funny incidents at work—the possibilities are endless.

"What brings you here?"

This question is especially useful for events such as a house party or a business meeting. Use the answer to continue the conversation. For example, a phrase like "I'm here to meet new people" means that this person is open to communication and new acquaintances. Perhaps you can share interesting events that are included in your calendar.

"What did you do today?"

Sometimes the answer to this question is standard and uninteresting. And sometimes they can reveal fascinating details about the interlocutor.

“How was the event (event)?”

If you know where the person has been before, use that to talk. For example, one of your friends or colleagues recently returned from a trip or was at an interesting conference. Ask him about this event.

"What are you doing this week?"

Since the question is about the future, ask it towards the end of the conversation so that you can say goodbye afterwards.

Be aware that you may be asked follow-up questions, so be prepared to answer them.

2. Give a compliment

For example, an option that works best in a women's company: “What a beautiful dress! It fits so well on you. Where did you buy it? and all questions that relate to accessories, hairstyles and appearance. Starting a conversation like “You look great! Did you have a good rest / went on a diet / started exercising? and so on also works well with men.

Compliments about the work done will be pleasant to everyone without exception. They work especially well with open and emotional people.

3. Use surrounding objects as a hook for a conversation

After meeting at the conference, say that you liked the speech of a particular speaker, indicate which moments made a good impression and ask the interlocutor what he thinks about it.

Use what is happening around you to talk, thus creating a comfortable atmosphere. After the ice melts, you can move on to more personal topics.

4. Ask for advice or ask for help

Often one question or a simple request for help can lead to a long, interesting and fruitful conversation.

Why does it work? Because people like to help. It gives them a sense of importance, a sense that they have done something useful. And admiring reactions to the answers make them feel like a senior mentor.

These may be questions on work topics. For example, you can say that you are currently busy with a new project and would like to know the opinion of a person, since he is an expert in this field.

Even if you don't really need help, ask for it anyway. Advice given by another person can open up interesting prospects for you, previously unnoticed.

The most interesting thing is that a normally silent and modest person can break his standard behavior and show himself from a completely different side. Some people just blossom when someone is interested in their hobbies.

5. Tell us something about yourself

What have you been doing in recent months? What new and interesting things did you learn? What goals do you want to achieve in the near future? Tell about it.

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