If your significant other lost his/her job and decided to just not work anymore, what would you do? If dishes could be synthesized perfectly, do you think there’d still be any place for chefs? These questions are great for dates, friends you know well, or person can be your boyfriend … If you had seen someone being robbed or assaulted, what are the chances that you would intervene? What was the most recent moment that changed your life in a major way? 3. If you could pick an age and just stay that age for as long as you’re alive, what age would you be? It’s St. Patrick’s Day, and someone pinches you for not wearing green. tells you he’ll / she’ll have a surprise waiting for you when you get back. 23. 7. Who should play me (as your best friend)? 25. If you could only eat salty snacks or sweet snacks for the rest of your life, which would you choose? What would you choose? Do you find it easy to make changes in life? If you had to eat the same thing for lunch every day, what would it be? 5. 6. Remember, these deep questions to ask a guy are for exploring deeply into topics like human nature, the future of the human race, and ethics. You Might Also Be Interested In: Questions to Ask a Girl – Discover the best of the best questions to ask a girl. It is more like a fun way to ask … What if the person you had to kill was innocent? Introversion & Extraversion. What’s something you’d do if you know you’d get away with it and no one would never know that it was you? You Might Also Be Interested In: Questions to Ask a Girl – Discover the best of the best questions to ask a girl. 15. And do you have a name already picked out? 10. Whether you're looking for questions to ask your significant other or your best platonic friend, the following deep questions can help you both understand each other better than ever. 18. Who do you look up to the most, and what qualities do you love about that person? If you had to get either a dog or a cat, which would it be? What do you think about freedom of speech? 3. The questions above are a great starting place. And may your gratitude and sense of humor influence everything else you do today. Now that you have 175 good questions to ask your best friend, see how many of them you can both answer. 19. 25. You must peep into the soul of your girl and know her like nobody else. Looking for deep things to talk about with your sig other? If you could go on a date – or just out to dinner — with a celebrity, who would it be? 11. Do you have a bad habit you wish you could change? 210 Questions to Ask Friends (For All Situations), 222 Questions to Get to Know Someone (Casual to Personal), Best Conversation Starters and Interesting Small Talk Topics, TIME Magazine, The Chicago Tribune, The Hill, MSN, WebMD. Notify me when someone responds to my comment. What was one of your favorite gifts as a child? This site uses Akismet to reduce spam. If you had to choose between the celebrity and a robot or your favorite book, what would you choose? How about ten years? 9. These questions to ask your best friends will help you get to know them even more! Do you think it’s possible to have a great life alone? 19. Who is the most important person in your life? How would you change the public education system? 14. What’s one thing about you that you’d never mention on a first date? Money aside, this question is … What do you most want to accomplish in your life? Did you ever feel like your parents were your friends? Have you gotten closer to the meaning of life in the last 10 years? Questions to Ask Your Best Friend. What was the last time when someone bluffed you? 21. 16. 25. Improve socially without doing weird out-of-your-comfort-zone stunts. https://www.rootreport.com/questions-to-ask-your-best-friend Do you think of yourself as more selfless or selfish? Should humans merge with the AI once it becomes an option? If you could earn any amount as your monthly income, what would that be and why? Why do you think older people have a harder time grasping new ideas? 23. 13. With some of the difficult questions to ask friends listed above, you might learn more about yourself than you do about your best friend. These questions are even deeper than the previous questions. Do you believe in karma? Find your significant other, friend, parent, brother, sister, travel buddy, stranger you met online… really, ANYONE you want to get a little closer with! 20. You’ve just won a home renovation package, but you have to choose between a complete reflooring and repainting (inside and out) of your home or upgrades for all your appliances, plus an extra (like a Nespresso machine or an above-the-range microwave). If you could only listen to one type of music (rock, alternative, jazz, classical, etc.) If you could change your appearance to that of the most beautiful person in the world, if it meant looking like a completely new person, instead of an improved you – would you do it? 1. If I have good news and bad news to share, which do you want to hear first? How would you finish this sentence if you were directing these words at me: “I wholeheartedly believe that you would make a great ______” or “I hope with all my heart that you finally _______”? Discover 71 silly and serious questions to ask friends and grow your bond. 5000? If you could magically change one thing in your life, what would it be? 21. When we met, what made you think I’d be a good friend? Would you forget a traumatic experience, if you could? If you could design the perfect life, what would it … What do you value most – comfort or personal growth? Deep questions will let you know to how extent you are connected to your friend and loved ones. 5. If you could choose between living for 1,000 years and living for only 50, which would you choose — and why? 20. Or what would you hope I did? See how you can go "from boring to bonding" in less than 7 words. by a waterfront and living in a spacious, light-filled, and beautifully furnished downtown apartment, so you could walk everywhere, which would you choose? What do you think are your best and worst qualities? In which situations do you think war is called for? When’s a good time to start getting serious about one’s health? 1). On your relationship: What did you think when you first met me? 18. 16. 11. Do you feel like your clothes are a part of your personality? Your new friend will get comfortable with time and even open up to some things you may not have known before. What do you do? You can ask the deep questions from your friends, family members, and the ones with whom you want to have an everlasting relationship. The following are some of the top deep questions to ask boyfriend and deep questions to ask girlfriend. What’s something you’d like to tell your parents that you would never dare to? What would that be? 17. What do you think about abiding the law vs. following your own moral code? What’s the angriest you’ve ever been? 9. What is something no one else knows about you? If I could change one thing about my life, what do you think it would be? 6. 12. It’s Christmas, and an attractive stranger walks up to you with a sprig of mistletoe and asks for a kiss — “just a little one .” What do you do? Use "conversational threading" to avoid awkward silence, Learn a proven technique to get past empty small talk. How would you feel if your spouse was in love with another person? Leave A Comment Uh-oh! 12. What kind of friend do you think you are to others? 8. Could you bring yourself to kill someone in self-defense? You probably have some idea as to the conversation territory your best friend would rather avoid, but you can still learn plenty about each other with the questions that follow. Or would you pretend to like it? 12. 2. What do you think is the meaning of life? Do you remember any character-defining moments from your childhood? 3. Do you ever wish you had different parents? If your next home could have one thing of your choice that your current home does not have, what would that thing be? 4. Spruce it … These deep questions are the perfect questions to get to know someone. 3. Is there ANYTHING that’s too serious to joke about? 16. Have you ever been arrested for anything? A courier has just arrived with news that you are related to royalty, and they want you to drop everything and head to the royal family’s country to be recognized. It is your turn to take some initiative and take the friendship between you to a next level. 3. Based on what you know about me, what do you think would make my life easier or more fun? What do you do when no one else is around that you’d rather most people didn’t know about? Would you do it if you knew for sure you’d never get caught? What happened? What do you think about veganism as a moral movement? 24. WARNING: These questions aren't all exactly PG (what fun would that be;). 5. 18. 22. Just like our deep questions to ask a girl, these questions are non gender specific. Would you donate an organ to someone you love? Let’s get started. Asking your friends deep or philosophical questions can kickstart some pretty interesting and enlightening conversations. What is your favorite season of the year? 19. If you had to get a tattoo, what would you get and where would it go? Where do you hope to be three to five years from now? If you were a four-course meal (salad/appetizer, pasta/soup, entree, dessert), what would you be? Do you think there's an alternative reality? Do you want to play hide and seek with your life in the time of crisis? Making conversation 9. Whether your goal is to learn something new, deepen the bond with a friend, or just have an interesting conversation, it can be hard to come up with questions to ask your friends. 16. Have you ever felt guilty about doing something good? What do you say? I hope you enjoyed these questions to ask friends and I know you might have jotted down a few of them. 10. 9. 6. When was the last time you tried to talk to me about something that was bothering you, and I did or said something that made you decide not to? And yes, I mean any age. That’s the risk you take when you make it your goal to know your best friend better. 8. 14. If I started dressing exactly like you – even trying to wear the same outfit every day – and then started talking and acting like you, what would you say to me? Social anxiety What do you see in yourself that you admire when you see it in other people? Do you think magic is evil, a hoax, or a natural extension of our nature? Spruce it … What’s something you think that you think no one else thinks? What is the first thing you usually notice about me when we meet (for coffee, chat, movies, etc.)? If you had to wear one outfit every day for the rest of your life, what would it be? 15. What family member do you feel closest to? This website uses cookies to function properly. There’s no limit when it comes to deep questions to ask your partner. If money were no object, what one thing would you buy for yourself to make life easier or more fun? Is there something you’ve wanted to do for a long time but haven’t yet? What actor would you like to play the starring role of your life? Before you head out one day, your S.O. Fun Questions to Ask – List of all the questions you can ask just about anyone. 17. Free training: Conversation skills for overthinkers. 13. Here, we’ve compiled a list of 107 deep questions that can serve as a start to some great conversations. 10. What are you most proud of? 2. Keep track of which long-distance relationship questions you’ve answered by downloading the PDF version of this list, available in the flowery box at the top of this page. If you could do anything for the rest of your life, what would that be? If you were an animal, what kind of animal would you be? It’s Halloween and your S.O. 5. If you were trapped on an island, would you rather resort to cannibalism or die of … Could you commit suicide if you knew it would save the lives of 100 other people? How old were you when you lost your virginity? 21. If someone you cared about voted for a candidate you strongly dislike, would you forgive that person? If you could instantly speak any second (or third, etc.) If you had to choose between living in a fully modernized castle (air conditioning, adequate heating, plumbing, wifi, etc.) 22. This post shows you the best deep questions to ask your boyfriend. Asking open-ended questions and leaving room for listening, storytelling, and answering questions in return fosters healthy conversation and allows two people to get to know each other more deeply. What’s the best thing about your life right now? Have you ever sent someone sexy photos of yourself? Have you ever in your life thought, “never again”? Again, you may see your best friend daily, … 3. 17. You just received a gift that reminds you of the best gift you’ve ever received — but this gift came from someone you hardly know, and that someone winked at you when handing you the gift. If you were traveling by yourself, where would you go and what would you do? 19. What stops you from lying and stealing? 9. If I won the lottery and was suddenly a half-billionaire, what do you think I’d do first? 1. If I was going on a date, and I showed you the outfit I was planning to wear, and you thought it was unflattering, what would you do? Ritualize deep conversation. If you could have sex with one famous person or celebrity, who would it be? If you look at your best friend sometimes and think, “Do you really know me that well?” or “What do I not know about you that I should?” it can’t hurt to ask some personal questions. 22. Improving your confidence For example in prison, or severely disabled, or maybe doing things you would never actually do in reality. 22. Or would you rather be left alone to process it? If you had to be stranded on a desert island with a celebrity, who would it be? What do you hope it will be? What do you do? 17. What was the last (or most memorable) gift you’ve received that you ended up donating or giving to someone else? Check out these 25 weird questions to ask your best friend: 1. Let’s be real: even marathon-callers can’t conquer 225 questions in a single video call. Pick from any of these 25 personal deep questions to ask your friend: 1. Are you happy with your body and showing it during sex? They will often lead to thought-provoking conversations that can tighten your bond. 7. It can be helpful to balance asking questions and sharing about yourself, so what your friend doesn’t feel interrogated. If you could have chosen your own name, what would it be? If you could ask the reaper to spare your loved one, what would you tell him? 17. Leading media outlets such as TIME Magazine, The Chicago Tribune, The Hill, MSN, WebMD, and 100+ more rely on SocialPro’s expertise in psychology. If you could eat one thing for dinner every day, what would it be? 25. 77). 13. Who was the last person to make you cry? And then there are friends who are fine with amicable silence but who also take the time to answer your questions thoughtfully. If someone who knew us both asked you whether I’d rather have a million dollars or a cool superpower, what would you tell them? If you were to die today, what would be your greatest accomplishments that you are most proud of? just left me for someone else, and he accidentally left his credit card in my apartment. If you had one day left to live, how would you spend it? Is there anything more I could do to make sure you know how much I appreciate having you as a friend? 20. Who is your favorite fictional character and why? Start improving your confidence, your conversation skills, or your ability to bond - in less than an hour. For more fun, deep questions to ask, check out these 250 conversation-starters and interesting questions that’ll keep your convo going. 76). 20. Being strangers, one person has to start the conversation, and if you are confident enough, you can take the lead. If you could play a friendly prank on any actor, whom would you prank and how? 19. 14. If you could go back and tell your childhood self something, what would it be? Below we’ve got some deep questions to ask that is far from light and fluffy icebreakers. What was the most difficult “goodbye” in your life? Has anyone ever mistaken you for someone else — and did they do something either of you regret? 21. Personal development 11. 25. What do you think about the current younger generation? 10. What is your weirdest fantasy, and what would you do if it came true? 23. What's the most times you've had sex in one day? 24. You may wish to find funny questions to ask your best friend, or some deep questions about feelings and opinions. If I told you one day that I had a superpower that made it unnecessary for me to pay rent (or pay for much of anything), what would you do? Is it more important to believe or to know? 7. 8. If I were to tell you I had a year to live, what would you do? What's the most ridiculous thing you ever said to someone you liked? Deep questions can help you both learn more about yourself, the other person, and the world. Where is the strangest place you've had sex? What’s the point in living, if you’ll end up dead anyway? What would you tell me? 22. Topics to talk about – If you are running out of things to talk about or if you are looking for something lighter than philosophical questions, try this one. Has any piece of art ever inspired you to change your life in some way? If you ended up in a coma for 10 years, still conscious but unable to communicate, would you want them to pull the plug? 18. 11. How is your relationship with your parents? What is your favorite thing about my home/living space? However… What behaviors do you despise in another person? https://www.womenshealthmag.com/life/a27973614/questions-to-ask-friends 6. One of you comments on the other’s sweater, and you’re off to a running start — jumping merrily from one tangent to the next. Questions to ask your best friend is a way through which you can explore the unheard things of each other’s life. Do you see us doing something together within the next five years? 5. 12. What's the longest time you've gone without sex? Have you ever done what you thought was the “right thing” with catastrophic results? What does your ideal life look like? If someone were to tell you, “Congratulations, you just won a lifetime supply of ______!” what would you want to hear in that blank? SocialPro works together with psychologists and doctors to provide actionable, well-researched and accurate information that helps readers improve their social lives. 107 Deep Questions to Ask Your Friends (And Connect Deeply) Loneliness You had other plans for the evening. Is it more appealing to have a career or to do odd jobs? When was the last time you just sat and talked to your best friend about anything and everything? 15. If you’ve always been completely honest with someone, and you had to lie to them to save their life, would you find it hard to do? 4. Have you ever reconciled with someone you were sure you’d never talk to again? Take this quiz and get a custom report based on your unique personality and goals. What challenges do you most want to overcome? Maybe you and your best friend don’t need much of a prompt to get a conversation going. I just spent way too much money on a new exercise machine, because it has all the features I want, and I didn’t want to wait for a sale. Follow on Twitter or read more. If you could visit any period in history, when and where would it be? Click to Grab the FREE Report: "Boring To Badass: Reinvent Yourself By Learning Self-Confidence Skills”, Questions to Ask Your Best Friend about Yourself, Personal Questions to Ask Your Best Friend, 105 Powerful Simple Pleasures You Should Never Take For Granted, 23 Couple-Approved Steamy And Fun Sex Games For Couples, 13 Signs A Married Man Is In Love With Another Woman, Is Your Husband Emotionally Unavailable? 4. If you were hoping to get a laugh and maybe share a few smiles with 20. What relationship shaped you the most when you were growing up? These deep questions to ask a guy Might Not Be ideal for your close friends (Whom with you are already very close), they are suitable for creating a strong bonding with a new guy you just met. If you only had those two options, would you rather make all drugs illegal, or make all of them made legal? How do you think porn affects our society? Is there someone in your life you really dislike? If life was nothing but constant pain, would it still be worth living? What about our relationship makes … In this post, I have listed out some interesting questions to ask your best friend. Where are you when you feel the most safe and comfortable? If you could have dessert every day, but it had to be same thing (every day), what would it be? bought a new perfume/cologne, and you think it smells terrible. Your guy friends are no doubt plays an important role in your life. 23. It’s important to not ask these questions too early on in your relationship as they can make someone uncomfortable. So feel free to use either set for some good deep questions. You walk in and find me holding it and looking as though I’m plotting something. If you won half a billion dollars from the lottery (assume you bought a ticket), what would you do first? If you could be driven around everywhere by a chauffeur, what vehicle would you want that chauffeur to drive? What's the funniest thing that's ever happened during sex? 2. 12. 7. 4. Fun Questions to Ask – List of all the questions you can ask just about anyone. 10. 6. Do you ever imagine yourself in very negative, but unlikely scenarios? 14. 14, If you had the chance to play a role in a movie with one of your favorite actors, but it involved a kissing scene, would you say “Yes.” Or would you rather just sit down with this actor and chat for half an hour over coffee (or something else)? Do you think bullies often see themselves as bullies? How do you wish you’d handled it? 2. Take the leap. What did you dream about last night? What would you change in your life if you knew that there was a god? 19. Do you ever wish you’d handled a situation differently? 13. 25. 1. Have you ever felt like you have no regrets in life? 20. 4. 24. Do you wonder if there really is a God? When searching this, I wasn't really sure I would find questions that would be interesting enough but surprisingly, I found really great ones that led to conversations that lasted all night! What would make it easier to tell me? 21. Here are some interesting and fun random questions to ask to get to know your best friend even better.