I love getting to know others — their stories, the way they think, and the way they experience the world. Whether you’re dating or want to get to know someone better, these questions can help guide your conversation and bring you closer!
How to Use This List
You can use this list any way you wish! Feel free to print them, rewrite them, forward them to a friend to fill out, or not use them at all. This list is as much yours as it is mine, so you have full creative freedom and rights!
Two options I’d recommend are: (1) Run through the list from beginning to end, OR (2) Randomly select a number from 1 to 105 and answer the question.
If you’re going to ask these questions live with a partner/loved one, I would recommend you take turns answering them first. I also made an effort to make the questions increasingly more intimate, though this is not entirely the case. When answering and asking these questions, be vulnerable. Getting to know someone is a process and when having intimate conversations, I recommend being honest and true to yourself. Take time to think of your response.
This list has birthed out of two personal experiences. First, in 2020, my coworkers and I transitioned to working remotely. As a healthcare worker, we were not used to having such distant connections. During our morning meeting via phone/zoom, I started asking daily questions so we could get to know each other more. I learned things about my coworkers I may not have otherwise and this helped us stay connected during the challenging time. Secondly, I have been thinking of ways to stay intentional when dating and getting to know others. While small talk has its place in the world, I often find myself lost — wanting to go deeper. To really understand someone. Hence, I started making a list of questions I love asking others to get to know them. *BOOM* — this list! Some of them are truly thought provoking and others are simply trying to understand someone’s personality.
Finally, I would love to add more questions to this list (which is why the title is 100+ haha), so if you have questions you’d add — please drop them in the comments!
105 Questions
- What’s your idea of a perfect day?
- What is a dream you have?
- Tell me about your family. How close are you with them?
- Have you been married or have any children?
- What are you looking for in life?
- What do you tend to spend too much money on?
- Do you have any debt?
- How are you with finances? Investments?
- Do you have any addictions or have you in the past?
- What movies can you watch over and over and not get tired of them?
- What type of music do you listen to? What was your top artist and/or song on Spotify this year?
- If you could only see one musical artist/group live this year, who would you see?
- What’s the first concert you ever went to?
- Did/do you play any sports? At what level?
- Do you like to watch any sports? To what extent?
- What’s one talent you wish you had? If you could wake up tomorrow with any talent or quality, what would you want it to be?
- Do you believe in marriage? Do you want to have a family of your own one day?
- Are there any kids in your family? How do you like spending time with them?
- Would you be interested in adoption?
- What are your top self-care habits?
- Have you read any books recently?
- What’s a book that changed your life or the way you see the world?
- What does a normal workday look like for you?
- What is your favorite thing about your current job?
- What do you wish you could change about your profession/current job?
- How do you define success?
- What do you do to keep active?
- What’s your relationship with social media?
- In what way(s) do you express yourself creatively?
- What kind of art do you like enjoy? Do you like theater and/or musicals?
- When did you last cry?
- Have you been to an art museum? What’s the last museum you went to?
- What’s one of your earliest memories?
- What is your best and worst childhood memory?
- What Harry Potter film/book is your favorite? (Alternatives: Lord of the Rings, Hunger Games, or your favorite series here!)
- If you could be any fictional character, who would you be?
- Who is your favorite superhero and why?
- Do you believe in God? An afterlife?
- What has your relationship with religion been like?
- Name 5 things on your bucket list.
- What place/country would you like to travel back to?
- If you could see any view from your bed, what would you want it to be?
- If you could go anywhere in the world next week and money were no limit, where would you go?
- If you could do any job except the one you have now without needing to fulfill the prerequisites and make the same money you do now, what would you choose?
- What is your favorite TV series?
- What can you watch reruns of?
- What’s the most memorable meal you’ve had?
- What is your favorite meal to cook?
- If you could eat only one meal for the rest of your life (and it were considered healthy), what would you choose?
- What makes you feel frustrated?
- What are your biggest pet peeves?
- How do you cope with stress?
- Who do you look up to in life?
- Whose relationship do you look up to? Of your friends and family, who do you think has the best relationship and why?
- What’s your biggest fear in life?
- Have you ever been to therapy?
- When is a time you struggled with your mental health?
- What is your greatest loss?
- What is the most physical pain you’ve been in?
- What’s one thing you want to improve about yourself?
- What’s something you wish you had done differently?
- Is there something that you’ve dreamed of doing but haven’t yet? What’s prevented you from doing it?
- What’s an opportunity you feel you missed?
- If you can take only one thing with you on a vacation besides your wallet and phone, what would it be?
- What’s one of the worst travel experiences you had?
- What would you consider unforgivable and why?
- Complete this sentence: “I wish I had someone with whom I could share…”
- Do you like to gamble?
- How often do you drink? To what extent?
- What’s your favorite holiday? How do you like to celebrate it?
- What’s a Halloween costume you remember wearing? If you could be anything this year, what would it be?
- What traditions do your family have? Are there any holiday traditions you want to start?
- Imagine the most comfortable you’ve ever been… Describe it to me.
- Imagine the most scared you’ve ever been… Explain it to me.
- If you could eliminate any emotion from your family, what would you choose?
- Describe your political beliefs.
- What makes you laugh really hard?
- Do you have any tattoos? If you had to get one tomorrow, what would it be?
- If you had to describe yourself as an element, what would you be and why? Be specific (i.e. not “water,” but are you an ocean, river, stream, waterfall, etc.).
- Do you prefer coffee or tea? Beer or wine?
- What does your dream home look like? Where would it be?
- Do you find value in personality tests or astrology? Why or why not? (What is your enneagram number? Myers Briggs?)
- What would you describe as your love language? (Words of affirmation, quality time, receiving gifts, acts of service, or physical touch.)
- When did you first drink?
- What drug(s) have you done? How often do you do drugs now?
- Have you ever smoked cigarettes?
- Describe yourself in high school.
- Do you like to dance? If you had to dance, what type would you want to learn?
- What’s the last vacation you went on?
- Where have you lived?
- What emotion tends to hold you back the most?
- If you could see any artist in the VIP section, who would it be (dead or alive)?
- Who would you most like to have dinner with (dead or alive)?
- What’s the most memorable concert you’ve ever been to and why?
- Would you describe yourself as an introvert or extrovert? Why?
- Describe your favorite hike or outdoor adventure you’ve been on.
- Do you prefer planning or being spontaneous?
- What’s something you’re afraid of in a relationship?
- Who was your first partner?
- Did you grow up with any pets? Would you want a pet/do you have one?
- Who are your three closest friends? Tell me about them.
- Who was your first crush?
- How important is sex life? Describe what it feels like and looks like to be intimate with someone else.
- Would you want to know in advanced how or when you’re going to die?
- How do you think your family and friends would describe you at your funeral?
Bonuses for Serious Daters
- In your opinion, why are you single?
- Are you looking for a relationship?
- What has your dating experience been like recently?
- What are you looking for in a partner?
- Have you ever been in love?
- Have you ever finished a chap stick before losing it? (Because this shows SERIOUS commitment.)
Suggested Reading
- Article: 36 Questions for Increasing Closeness (45 minutes)
- Article: 10 Questions Happy Couples are Constantly Asking Each Other
- Book: If… (Questions For The Game of Life), by Evelyn McFarlane and James Saywell
Feature Photo Image: Canva
