: 11, 2026 10:36 pm : (!!Flirt!!^) get to know people
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Learn why people trust wikiHow QUESTIONSASKING QUESTIONS 100 Questions to Ask People in Any Situation Download Article Executive communication expert Brenden Kumarasamy shares what to ask to get to know someone on a deeper level Co-authored by Brenden Kumarasamy and Dan Hickey Last Updated: June 4, 2026 Fact Checked Ice Breakers |Colleagues |Friends & Family |Partners |Students |Teams |Lighthearted |Deep |Getting to Know Someone Asking questions is the cornerstone of getting to know someone better or starting an engaging conversation. Knowing exactly what to ask might seem tricky, though, but that’s where we come in! We interviewed various communication experts to share the best questions and ice breakers for colleagues, friends and family, partners, and more that’ll help you grow closer and spark a deeper connection.
We’ve also got exclusive pro tips on how to get to know someone to help you navigate any conversation. What are some good questions to spark connection? Executive communication expert Brenden Kumarasamy suggests asking questions that you would want to be asked in order to get to know someone. He suggests questions such as: What are you passionate about? What are you working on that's interesting to you? What's something you really love to do outside of work? What's your purpose? What’s a memory you’ll never forget? Questions to Break the Ice Download Article Ask simple but engaging questions to break the ice with new people. These ice breaker questions are perfect for starting to get to know someone in any setting—they’re interesting, non-invasive, and make the perfect jumping-off point for deeper conversation. The next time you’re not sure what to ask, try: If you had to eat one meal every day for the rest of your life what would it be? If you had to teach a class on one thing, what would you teach? What is your favorite time of the day and why? If you could pick up a new skill in an instant what would it be and why? If you could be in any movie, what would it be and what character would you play? Do you have any hidden talents? What can you do? Have you ever been out of the country? If you could have a superpower, what would it be and why? If you could be any fictional character, who would you be? What was your first job? Are you more of a morning person or night owl? What’s your favorite holiday? Do you prefer coffee or tea? Meet the wikiHow Experts Brenden Kumarasamy is an executive communication and public speaking coach with over 6 years of experience helping professionals master the art of communication. Kirin Dejonckheere is a certified life coach based in NYC who helps each client learn to connect with others and build the life they desire. Mark Rosenfeld is a dating and relationship coach with over 10 years of experience specializing in helping people connect and find and keep extraordinary relationships. Emyli Lovz is a dating and relationship coach with 14 years of experience helping men and women meet and maintain healthy relationships. Dr. Marisa G. Franco is a friendship and belonging expert who offers and speaks about research-backed, actionable advice for improving connection. Questions for Colleagues Download Article Deepen your connection with your coworkers through friendly, professional questions. According to certified life coach Kirin Dejonckheere, a great way to get to know your coworkers is to “bring the conversation outside of work, like ‘How do you spend your time outside of work?’ or ‘What are some professional or personal goals that you're excited about?’ As a co-worker, you have to keep it appropriate, so stay focused on listening and asking the right questions.”[1] What’s something you’re proud of accomplishing? What’s your favorite way to relax? What’s one skill you’d love to learn? What’s the best gift you’ve ever received? What’s your favorite tradition? What’s your favorite subject or topic to learn about? What’s the best piece of advice you have ever been given? What would you like to do when you retire? What is your favorite time of the day and why? What is your favorite sport or physical activity? What is the best perk you have ever enjoyed at a job? If you could magically become fluent in any language, what would it be? If you could eliminate one thing from your daily routine, what would it be and why? Questions for Friends & Family Download Article Keep conversations with your loved ones fresh by asking new and intriguing questions. You may think you know everything about your closest friends and relatives—but do you? There’s always more to learn about a person, including those in your inner circles. Discover something new and start a stimulating chat with questions like: Are there any household chores you secretly enjoy? Which ones, and why? Can you tell when someone is lying? Do you have any irrational fears? What’s your favorite family tradition? What’s a meal that brings back good memories? What’s your favorite holiday activity? What’s something you’re grateful for right now? What’s a recent moment that made you smile? What’s your favorite way to spend time together? Have you ever actually kept a New Year’s Resolution? Have you ever met one of your heroes? How long can you go without checking your emails or texts? What are you bored of? Questions for Partners Download Article Ask curious questions about your partner to grow closer. “Ask questions about their upbringing, their likes, their dislikes, their wants, and their needs,” advises dating and relationship coach Mark Rosenfeld. “Asking good questions and getting curious can help” you deepen your bond.[2] Dating and relationship coach Emyli Lovz offers questions like: What's the best mistake you've ever made and why?[3] What's something you're sure you would never do, but secretly wish you had the guts for?[4] What do you think is the meaning of life?[5] What’s something that has shaped who you are? What was your proudest moment from the past twelve months? What was your very first job?
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