Questions to Ask to Get to Know Someone: 240+ Prompts for Work, Dating, Friends & More

• Start light. Move from easy topics to personal stories as comfort grows.
• Match the context. Choose “Work & Team” at the office; “First Date” in romantic contexts, etc.
• Invite stories. Ask openers like “What makes you say that?” or “Can you tell me more?”
• Model the vibe. Answer first sometimes to set a friendly tone.

1. What’s something small that made your day better this week?
2. Which emoji do you overuse and why?
3. What’s your go-to comfort food?
4. What’s one song you never skip?
5. Are you an early bird, night owl, or “whenever I must” person?
6. Coffee, tea, or something else entirely?
7. What’s a hobby you picked up recently?
8. What’s your most-used app right now?
9. What weekend activity do you look forward to?
10. What small skill are you oddly proud of?
11. Which city felt instantly “you” when you visited?
12. What’s the best thing you’ve watched lately?
13. What’s your favorite way to recharge?
14. What podcast or channel would you recommend?
15. What’s something you’re learning this month?
16. What’s your current wallpaper (phone/desktop) and why?
17. What’s a smell that brings back memories?
18. What’s a simple pleasure you never skip?
19. What’s your underrated life hack?
20. Which season are you living for right now?

1. If animals talked, which species would be the sassiest?
2. What food do you passionately dislike for no logical reason?
3. Which movie would be better if it were a musical?
4. What’s your funniest autocorrect fail?
5. Which fictional character would you hire as a life coach?
6. What fashion trend do you secretly miss?
7. What’s your most hilarious kitchen disaster?
8. What everyday task should become a competitive sport?
9. If you had a nonsense superpower, what would it do?
10. What’s your go-to “bad” joke?
11. What’s the weirdest thing you believed as a kid?
12. Which snack would you name your autobiography after?
13. What’s your most dramatic lost-phone story?
14. If you had a theme song when you entered rooms, what would it be?
15. What’s your most chaotic travel mishap (that’s funny now)?
16. Which object in your house would be the snarkiest if it could talk?
17. What’s a humble brag you’ll allow yourself today?
18. What’s a food combo you love that others judge?
19. What’s the most “you” meme template?
20. Which celebrity would you cast to play you in a sitcom?
21. What’s your funniest misunderstanding while texting?
22. What’s your emergency karaoke song?

1. What kind of work gets you into flow?
2. How do you like to receive feedback?
3. What’s a small work habit that makes a big difference?
4. Which tool or shortcut saves you the most time?
5. What’s a meeting ritual you actually enjoy?
6. What skill are you leveling up this quarter?
7. What advice from a past manager still guides you?
8. What makes collaboration easy with you?
9. What’s a project that taught you a lot (even if it was hard)?
10. When is your best thinking time?
11. What myth about your job do people get wrong?
12. What boundary protects your focus?
13. What kind of teammate brings out your best?
14. What do you wish every new hire knew?
15. How do you like to start your workday?
16. What professional risk paid off?
17. Which cross-functional skill are you building?
18. How do you celebrate team wins?
19. What motivates you when energy is low?
20. What’s an underrated part of your role?
21. What’s one thing you automated or simplified?
22. What learning resource would you recommend?
23. What keeps you at a company long-term?
24. What’s something you’re proud of this quarter?

Facilitator tip: Let people choose numbers 1–24 at random for playful participation.

1. What’s a tiny green flag you notice quickly?
2. What does a good weekend look like to you?
3. What food are you always in the mood for?
4. What kind of humor gets you laughing?
5. What’s a spot you’d love to show someone in your city?
6. What’s your love language for giving and receiving?
7. What’s the last thing you did that felt brave?
8. What’s your idea of a great low-key date?
9. What book or movie genuinely changed your mind?
10. What do you value in relationships that people overlook?
11. How do you prefer to communicate between dates?
12. What’s your favorite way to stay active?
13. What makes you feel most cared for?
14. What fun tradition would you start with a partner?
15. What’s your stance on spontaneous trips?
16. What’s a non-negotiable for you?
17. What daily joy would you want to share?
18. What red flag have you learned to spot early?
19. What does quality time look like for you?
20. What’s a simple date idea you love?
21. What’s a small kindness you won’t forget?
22. What makes a conversation feel effortless?
23. What’s a relationship lesson you’re glad you learned?
24. What’s something you’re excited about this year?

1. What’s your ideal game night lineup?
2. What’s a recipe you’ve nailed?
3. What song gets you moving every time?
4. What last-minute plan turned out great?
5. What’s your “two truths and a lie” specialty?
6. What trip would you love to plan with friends?
7. What’s your perfect lazy Sunday?
8. What tradition do you have with friends?
9. What’s your favorite local hidden gem?
10. What small gift do you love giving?
11. What fun challenge would you try together?
12. What do you collect or geek out about?
13. What’s your signature party snack or drink?
14. What’s a music artist you’d see live again?
15. What’s a photo that always makes you laugh?
16. What’s your favorite icebreaker game?
17. What’s your best “host tip” for cozy vibes?
18. What’s your go-to conversation starter with new people?

1. What family meal feels like home?
2. What game do you never get tired of?
3. What bedtime story or show do you both enjoy?
4. What new skill are you learning together?
5. What outdoor activity is always a win?
6. What’s a silly tradition in your family?
7. What’s the best rainy-day activity?
8. What chore do you secretly like?
9. What kind thing did someone do for you this week?
10. What should adults ask kids more often?
11. Where would you love to explore as a family?
12. What childhood story do you love telling?
13. What’s your favorite “quiet time” activity?
14. What’s a new food you tried and liked?
15. What’s a song everyone can sing together?
16. What helps when big feelings show up?
17. What’s your favorite holiday tradition?
18. What makes a house feel like home to you?

1. What topic could you teach the class for 5 minutes?
2. What helps you focus when it’s tough?
3. What project made you feel proud?
4. What study tip do you wish you knew earlier?
5. How do you like to show what you learned (talk, write, build, draw)?
6. What question do you wish teachers asked more?
7. What’s a good way to start group work?
8. What historical figure would you interview and why?
9. What small goal will you set for this week?
10. What makes a classroom feel safe for you?
11. What book or article surprised you?
12. What creative way would you present a project?
13. What’s a topic you’d love to explore deeply?
14. What helps you remember new concepts?
15. What’s your favorite way to take a break?
16. What’s a moment you learned from a mistake?
17. What’s a subject you appreciate more now than before?
18. Who’s someone you learn from outside of school?

1. What are you up to later?
2. What’s your current hyper-fixation?
3. Send a photo of something that made you smile today?
4. What’s your underrated life hack?
5. What’s your ideal 10-minute break?
6. What song matches your mood?
7. What’s a hill you’ll die on (playfully)?
8. What tiny goal will you try tomorrow?
9. What notification do you actually like getting?
10. What’s your favorite meme format right now?
11. What question do you wish people asked you?
12. What’s something you’re grateful for today?
13. What’s your current read/watch/listen?
14. What’s a win you want to celebrate?
15. What’s one thing you’re curious about me?
16. What should we plan this week?

1. What does a “good life” mean to you right now?
2. Which values guide you when it’s hard?
3. What habit changed your days?
4. What cause do you care about and why?
5. What’s your relationship with ambition?
6. What boundary are you proud of setting?
7. What do you do when you feel overwhelmed?
8. What does rest look like for you?
9. What kind of community do you look for?
10. What makes a place feel like home?
11. When do you feel most creative?
12. What fear have you befriended?
13. What does success mean in this season?
14. What’s something you’ve unlearned recently?
15. What tradition would you like to start?
16. What does “showing up” for people look like to you?
17. What role does money play in your version of freedom?
18. What’s a daily practice that grounds you?

Offer an easy pass: “Totally okay to skip anything here.”

1. What’s a moment that quietly changed you?
2. What story are you still making sense of?
3. When do you feel most like yourself?
4. What do you want to be remembered for?
5. What painful experience grew you?
6. What belief have you re-examined lately?
7. What does forgiveness look like to you?
8. What’s something you wish you’d said earlier in life?
9. What’s your relationship with uncertainty?
10. What are you learning about love?
11. What risk would you take again?
12. What does courage look like for you right now?
13. What are you grateful you let go of?
14. What dream are you quietly working toward?
15. How do you know you can trust someone?
16. What does healing look like for you?
17. What part of your story are you proudest of?
18. What would your younger self be surprised by today?
19. What’s a question you wish people asked you more often?
20. What’s something you’re still learning to accept?

This-or-That (Rapid Fire)

• Sunrise or sunset?
• Mountains or ocean?
• Books or podcasts?
• Call or text?
• Plan ahead or go with the flow?
• Sweet or savory?
• City loft or country cabin?
• Art museum or live concert?
• Coffee at home or café crawl?
• Board games or video games?
• Early flight or late train?
• Comedy or thriller?
• Cats or dogs?
• Cook in or dine out?
• Road trip or staycation?
• E-books or paperbacks?
• Solo focus or team brainstorm?
• Workout class or outdoor run?
• New recipe or trusted favorite?
• Introvert night or extrovert night?
• Neat desk or creative mess?
• Long walk or quick workout?
• Playlist or podcast?
• Photo memories or journal entries?

1. …have unlimited travel time or unlimited travel budget (but limited time)?
2. …master every language or master every instrument?
3. …live by the beach or in a forest?
4. …always be 10 minutes early or 10 minutes late?
5. …cook for friends or be cooked for?
6. …host the party or be the VIP guest?
7. …rewatch a favorite show or try a new one every time?
8. …have a calm morning or a slow evening?
9. …work four intense days or five balanced days?
10. …have endless curiosity or endless patience?
11. …save for one big trip or do many smaller ones?
12. …get great advice or great encouragement?
13. …be famous for something silly or respected for something serious?
14. …always say what you think or never speak unless asked?
15. …live in the past for a day or the future for a day?
16. …have a personal chef or a personal trainer?
17. …be great at small talk or great at deep talk?
18. …take a risk now or wait for perfect timing?

FAQs about Questions to Ask to Get to Know Someone

What are the best questions to ask to get to know someone?

Start with light, open-ended questions about daily life and interests. Move gradually toward personal values and stories. The best questions invite stories—not one-word answers.

How do I avoid awkwardness?

Offer an opt-out (“skip anything”), match the other person’s energy, and answer first occasionally to set a friendly tone.

What questions should I avoid?

Avoid intense topics too early (money, politics, trauma) and anything the other person seems hesitant about. Curiosity should feel safe, never invasive.

How do I keep a conversation going?

Reflect a detail (“you mentioned…”) and ask a gentle follow-up (“what happened next?”). Aim for a rhythm of ask → listen → connect → follow-up.

What if we disagree?

Stay curious, not combative. Ask how they formed that view and what experiences shaped it. Look for common ground or shared values.

Wrap-up & Next Steps

Use these questions to ask to get to know someone as a map, not a script. Pick a lane—work, dating, friends, family, or classroom—start light, and follow the stories. Want more engagement? Add a “copy all” button per section, offer a printable PDF, and link to related resources like icebreaker games, first date ideas, or conversation starters for work.