100+ “How well do you know me” questions to ask partners, friends, and family

Asking questions about yourself can be a revealing way to understand how others see you. Plus, it could also be a fun or even surprising path to deeper connection.

Whether you're chatting with your partner, sharing stories with friends or workmates, or reconnecting with family, the right questions can build emotional closeness and laughter.

The key is keeping it light, respectful, and appropriate to the relationship. Starting with “what,” “who,” “where” and “am I” questions helps create comfort before moving into more personal or reflective territory.

“How well do you me questions” for romantic partners

Start simple:

• Am I more of a morning person or a night owl?

• What’s my favourite food to order on a Friday night?

• Who’s my celebrity crush I joke about the most?

• Where would I go on my dream holiday?

• What’s my favourite thing to do on a rainy day?

Get reflective:

• What’s something that always cheers me up?

• Who do I turn to when I need honest advice?

• Where do I go when I want to clear my head?

• Am I someone who likes surprises, or not really?

• What’s one value I talk about often?

Add fun and laughter

•  What weird snack combo do I secretly love?

• Who’s more likely to cry during a movie - me or you?

• What’s the most ridiculous thing I’ve ever done on a dare?

• Where do I always lose my keys?

• Am I more likely to win a trivia night or a dance-off?

Questions to ask your best friends

Start simple

• What’s my go-to coffee or tea order?

• Who was my first big crush?

• Where did we first hang out, and what do you remember about it?

• Am I the planner or the spontaneous one in our friendship group?

• What’s a movie or show I’ve rewatched too many times?

Get reflective

• What’s something you think I’m secretly really proud of?

• Who do I look up to or admire most?

• Where do I seem most confident in life?

• Am I more likely to give advice or just listen when someone’s struggling?

• What’s one way I show love without using words?

Add fun and laughter

• What’s the most bizarre opinion I defend passionately?

• Who would play me in a sitcom about our lives?

• What’s the weirdest compliment I’ve ever accepted?

• Where would I absolutely thrive as a reality TV contestant?

• Am I more likely to start a spontaneous road trip or binge-watch a whole series in one sitting?

Questions to ask new friends

Start simple

• What do you think my ideal weekend looks like?

• Who do I remind you of (celebrity or fictional character)?

• Where do you think I’d rather spend time—a beach, forest or city café?

• Am I more into books, podcasts or movies?

• What food would you guess I can’t stand?

Get reflective

• What vibe do I give off when you first meet me?

• Who do you think I’m closest to in my life?

• Where do I seem most in my element?

• Am I more of a dreamer or a realist?

• What’s something I seem to care a lot about?

Add fun and laughter

• What random skill do you think I secretly have?

• Who would I challenge to a lip sync battle—and win?

• What’s something about me that would go viral online?

• Where do you think I’d accidentally end up if left unsupervised?

• Am I more likely to start a podcast or open a quirky café?

Questions to ask your immediate family members

Start simple

• What was my favourite toy or game growing up?

• Who was my best friend in primary school?

• Where did I always want to go on holidays as a kid?

• Am I more like Mum, Dad, or someone else in the family?

• What food did I always ask for at dinner?

Get reflective

•  What’s something you think I’ve always been good at?

• Who in the family do I share the most traits with?

•  Where have you seen me grow the most?

• Am I someone who shows emotions easily, or not really

• What’s one tradition I still care about?

Add fun and laughter

• What’s the weirdest thing I was obsessed with as a kid?

• Who used to tease me the most in the family?

• What’s one chore I always avoided?

• Where did I hide my snacks or lollies?

• Am I the family peacekeeper, instigator, or wildcard?

Questions to ask cousins and extended family

Start simple

• What do you think is my most obvious personality trait?

• Who in the family do I act most like?

• Where do you picture me living my “dream life”?

• Am I the cousin who keeps in touch or goes MIA?

• What holiday or event do I never miss?

Get reflective

• What’s something you’ve always associated with me?

• Who do you think influenced me most growing up?

• Where do I fit in the “family personality” chart?

• Am I more of a listener or storyteller at gatherings?

• What’s one moment we shared that stuck with you?

Add fun and laughter

• What’s the silliest thing I believed as a kid?

• Who did I think was the “cool” aunt or uncle growing up?

• What’s my most dramatic family group chat moment?

• Where would I totally take over as party planner?

• Am I more likely to win “Most Likely to Start Drama” or “Most Likely to Bring Snacks”?

Questions to ask colleagues about yourself

Start simple

• What’s something I always say during meetings?

• Who do I go to first when I need a second opinion?

• Where’s my usual spot in the office or during events?

• Am I more of an early bird or last-minute deadline hero?

• What’s my desk, workspace, or virtual background known for?

Get reflective

• What’s one thing you think I take great pride in?

• Who do I collaborate best with?

• Where do I bring the most value to the team?

• Am I the problem-solver, peacekeeper or energiser in the group?

• What’s something I do that sets the tone for others?

Add fun and laughter

• What’s the most “me” thing I’ve done at work?

• Who would I be in The Office sitcom?

• What’s my unofficial job title around here?

• Where would I hide if a surprise birthday party was being planned for me?

• Am I more likely to organise a team lunch or accidentally double-book my calendar?

Bonus funny “how well do you know me” questions

• What food combo do I love that horrifies most people?

• Who do I impersonate way too often for no good reason?

• Where would I accidentally fall asleep (and pretend it was intentional)?

• Am I the person who texts back straight away or never?

• What item in my bag, car or drawer would surprise you the most?

• What would I name a pet I’m clearly not responsible enough to own?

• Who would I panic-text if I got stuck in an elevator?

• What fictional job suits me better than my real one?

• Where would I thrive in a zombie apocalypse—or would I?

• Am I more likely to forget my wallet, my keys, or both at once?

Final thoughts

“How well do you know me” questions are a gentle and often joyful way to strengthen relationships.

Whether you’re sharing a laugh, uncovering shared memories or learning something new, these questions invite people to connect more deeply and authentically.

Choose your questions based on the setting and the relationship, and always approach the conversation with curiosity and kindness. And if deeper issues arise during your chats - whether it’s about identity, boundaries, communication, or something else - a therapist can support you in exploring those with care.