100 Questions & Conversation Starters for Any Situation

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?

Section 1 of 9:

Questions to Break the Ice

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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.

Section 2 of 9:

Questions for Colleagues

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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]
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Expert Source

Kirin Dejonckheere
Certified Life Coach

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- 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?

Section 3 of 9:

Questions for Friends & Family

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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?

Section 4 of 9:

Questions for Partners

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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]
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Mark Rosenfeld
Dating & Relationship Coach

Expert Interview} Dating and relationship coach Emyli Lovz offers questions like:
- What's the best mistake you've ever made and why?^{[3]
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- What's something you're sure you would never do, but secretly wish you had the guts for?^{[4]
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  Emyli Lovz
  Dating and Relationship Coach
  
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- What do you think is the meaning of life?^{[5]
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  Emyli Lovz
  Dating and Relationship Coach
  
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- 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?
- What’s the best compliment you’ve ever received?
- What helps you feel grounded?
- What’s a memory you’ll never forget?
- What beliefs from your parents did you inherit that you want to keep?
- If you could do it all over again, would you still pick the same career?
- What’s an embarrassing moment from your past that you can laugh about today?
- Tell me about the most sentimental object you own (or remember having). What did it mean to you?

Section 5 of 9:

Questions for Students

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Encourage students to open up with friendly questions about learning. Whether you want to get to know a student better or to help your students connect with each other, approachable questions about academics, the school environment, and their personal interests are a great place to start. These conversations can also help boost enthusiasm for the school year, too!
- What subject do you enjoy the most right now?
- What’s something new you learned recently?
- Who is someone you look up to?
- If you could design your own class, what would it be about?
- If you could start a club, what would it be?
- What’s one thing you’re really good at?
- Do you like working in groups or by yourself?
- What’s your favorite way to learn?
- What makes a class fun for you?
- What’s something you’re excited about this year?
- What kind of invention would you create to solve a problem?
- What’s something you want to accomplish in the next five years?

Section 6 of 9:

Team-Building Questions

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Foster a cohesive working relationship with work-oriented questions. Good team members know how to support each other and communicate effectively, but you can’t just guess at how to do that—you have to ask! Use questions like these to learn how your teammates can work together the best to achieve your goals (and enjoy your work while you’re at it).
- What’s one thing that helps you stay focused?
- What does a productive day look like to you?
- What’s a skill you want to improve this year?
- How would you describe your job to a five year old?
- What’s one thing that motivates you?
- Is it better to be late for work or to leave early?
- What’s your preferred way to communicate?
- What helps you feel supported at work?
- Would you rather live close to work or at work?
- What’s something that helps you reset after a busy day?
- What is the best piece of advice you have ever gotten at work?
- Do you prefer working from home or the office?

Section 7 of 9:

Funny & Lighthearted Questions

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Try a simple but silly question to loosen up (and get a laugh!). You can learn a lot about a person from their sense of humor, so ask some funny and unserious questions to help them let their guard down and reveal their quirky side. Plus, these questions are sure to lead to some entertaining followup conversations!
- What’s your go-to dance song?
- What’s the best insult you can think of?
- Which celebrity do you think you’d be friends with?
- What is your most-used emoji?
- What fictional place do you wish existed?
- What is the weirdest thing you have ever eaten?
- What are your most random pet peeves?
- What’s the worst musical instrument to listen to?
- If you had 25 hours in a day, what would you do with your extra hour (besides sleep)?
- What’s your favorite pattern?
- What’s one law you wish existed?
- What’s your best animal impression?

Section 8 of 9:

Deep Questions

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Ask the big questions about life, relationships, and priorities to see someone’s real self. If you’ve already established a rapport with someone but want to know them on a deeper level, ask them hard-hitting questions about themselves and what they think is important in life. Friendship and belonging expert Dr. Marisa G. Franco recommends questions that increase vulnerability, such as:
- What do you look for in a friend?^{[6]
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  Friendship and Belonging Expert
  
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- What are some things that most of your friends have in common?^{[7]
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- What are some things people can do to make you feel valued or supported?^{[8]
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- What kind of things excite you or make you really happy or make you feel passionate?^{[9]
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- What has brought you joy lately?^{[10]
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- Who has had the biggest influence on your life?
- What’s one rule you try to live by?
- What’s the hardest thing you’ve ever done?
- What’s something you’ve learned the hard way?
- What are you most grateful for?
- What’s one thing you’d tell your younger self?
- What’s a challenge that shaped who you are today?

Section 9 of 9:

Getting to Know Someone

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1
Ask questions that you would want to answer. “Write down the questions you wished other people asked you and ask that to other people,” recommends executive communication expert Brenden Kumarasamy. “For example, ‘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?’”^{[11]
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Expert Source

Brenden Kumarasamy
Executive Communication Expert

Expert Interview} Chances are that if you would want to be asked a certain question, other people would too!
2
Be a good listener after you ask a question. Communication coach Kamryn Reynolds says active listening is “the biggest thing” when it comes to getting to know a person. “Ask them a question, get them going on it and keep bouncing around until [the conversation] hits something that they are passionate about.”^{[12]
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Kamryn Reynolds
Communication Coach

Expert Interview} Then, licensed counselor Sabrina Grover, LMSW, advises “being present in the moment” and “not thinking about what you’re going to say next.”^{[13]
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Sabrina Grover, LMSW
Licensed Counselor

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- Wait until you hear something interesting, relatable, or surprising that elicits a natural response from you. That way, you can really absorb what the person is saying and find common ground to build a relationship on.
3
Remember to be yourself and have fun. Communication therapist Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP, suggests “allowing yourself to let your hair down and enjoy the company. Ask questions, get to know them on a personal level, engage in meaningful conversation and partake in activities where you feel like you are your best self.”^{[14]
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Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP
Communication Therapist

Expert Interview} After all, when you’re open and willing to share your true self, other people will get to know you, too!