Deep & Serious Questions to Ask
Ask these deep questions to truly connect with them on a deeper level. Studies show that participating in “reciprocal self-disclosure” (revealing personal information to each other) increases feelings of closeness between two people. These thoughtful questions will encourage the two of you to engage in this type of reciprocal self-disclosure, which can increase your emotional intimacy and help you get to know each other even better. What’s the best piece of advice you’ve ever received? Where in the world do you feel the happiest? What are your favorite and least favorite things about yourself? What are you most insecure about? What would you say is the biggest life lesson you’ve ever learned? What 3 things are you most grateful for? Is there a single person in your life you feel the closest to? Who is it? Who is the person you admire most? How do you think your closest friends would describe you? Do you think it’s different from how you’d describe yourself? Do you have any friends you’ve fallen out of touch with that you miss? What’s holding you back from reconnecting with them? What qualities do you seek out in friends and romantic partners? What boundaries are non-negotiables for you? Would you say you’re more of an optimistic or pessimistic person? Do you consider yourself more of an introvert or extrovert? Do you forgive others easily, or do you find it hard to move on from things? What do you do to cheer yourself up when you’re feeling down or stressed? How do you like to be supported when you’re going through something difficult? What does the perfect weekend look like to you? What is the toughest thing you’ve ever been through? Did it teach you something valuable? Do you believe in the supernatural at all? Or do you think there’s only material reality? Does getting older scare you? If you had to make a bucket list, what would you put on it? If you only had one day left to live, how would you spend it? What in life would you say you’re most passionate about? What activities make you feel most alive? When do you feel most like your true self?
Flirty & Romantic Questions to Ask
Ask these romantic questions to learn more about your compatibility. Sanders suggests asking your crush or significant other about their romantic history and preferences. Talking about love and romance in this way can help create a flirty vibe between the two of you, and it can also help you each understand what the other is looking for in a relationship. When was the first time you fell in love? What was it like? If you had to describe the feeling of falling in love in one sentence, what would you say? What was the toughest break-up you’ve ever been through? Why do you think it was so hard? What was the worst online dating experience you’ve ever had, and how did you deal with it? Do you think everyone has one soulmate, or do you think people have multiple? Do you believe in love at first sight? What do you think your love language is? What’s your communication style in a romantic relationship? What does romance mean to you? Do you like big displays of affection, or do you prefer more low-key romantic gestures? Do you prefer casual or fancy date nights? Do you think you have a specific “type,” or are you attracted to lots of different types of people? What are some personality traits that you find attractive? Do you prefer monogamy, or open relationships? Do you hope to get married to someone someday? What would your dream wedding look like? How connected are emotional intimacy and physical intimacy for you? Do you need to have one to enjoy the other? What’s your favorite type of kiss? How often do you prefer to be physically intimate when you’re in a relationship? What physical qualities do you find most attractive in another person? If you could plan the perfect romantic date, what would it look like? What was your first impression of me when we met? When was the first moment you realized there was chemistry between us? What song would you say is “our song”? What is your favorite memory of our relationship so far? What things about me do you find the most attractive? When do you feel most beautiful or attractive?
Cute & Fun Questions to Ask
Ask these questions to get a fun convo going. If you’re on a date together, talking on the phone, or even texting, you might want to stick to these cute, lighthearted questions. This is a great way to create a fun vibe and keep the conversation flowing! If you could switch lives with a celebrity, who would you choose? If you could live in a fictional world from a movie, TV show, or book, which one would you choose? If you could only watch one movie for the rest of your life, what would it be? If you could only listen to one playlist for the rest of your life, what songs would you put on it? Do you have a favorite book? A least favorite? Who is your favorite fictional character? What actor would you choose to play yourself in a movie about your life? What superpower would you choose to have? What are your favorite and least favorite pizza toppings? What are your top 3 favorite flavors of ice cream? If you could only eat one type of food for the rest of your life, what would you pick? What is your go-to late night snack? What is your go-to coffee shop order? What is your favorite meal of the day? Who was your first celebrity crush? If you won the lottery tomorrow, what’s the first thing you’d do with the money? If you could live in any city in the world, which would you pick? What’s your favorite holiday? What’s your favorite season of the year? Do you have any pet peeves? Would you rather speak every language in the world, or be able to play every instrument in the world? What’s your favorite gift to receive? Are you more of a cat person or dog person? Are you more of an early bird or night owl? Do you consider yourself outdoorsy, or do you prefer indoor activities? What is your go-to karaoke song? What is your favorite theme park ride? What has been the most embarrassing moment in your life so far? Do you have any nicknames? If so, do you like them? Do you have any hot takes or controversial opinions?
Questions about Goals & Values
Ask these questions to learn more about what they want out of life. Quinlan recommends talking about these things with a crush or significant other to make sure you’re in alignment with each other, and so that you can encourage each other to go after your dreams. How do you define success? When you picture your life in 5 years, what does it look like? What would you say has been your greatest achievement in life so far? Are you happy with your current job? What is your dream career? What’s the biggest professional risk you’ve ever taken? Did it pay off? What’s the biggest career setback you’ve ever faced? How did you overcome it? Do you have any passion projects that you’ve always wanted to pursue? What’s a short-term goal that you’d like to accomplish in the next year? Are there any areas of your life that you think you need to change to meet your goals? What’s your favorite way to recharge after a busy work week? What goal would you go after if you had unlimited time and resources? What does having a good work-life balance mean to you? How important is it to you to have a family? Do you want to have children? When you picture your future family life, what does it look like? If you had to list your top 3 core values, what would they be? How important is religion or spirituality to you? Do you have a specific belief system or follow a specific religion? Do you think it’s important to have a similar worldview to someone to be close to them? What qualities do you think make someone a good person? Do you enjoy giving back to your community? What’s your favorite way to do this? What social or political issues are you most passionate about, and why? Do you think it’s important to travel a lot in life?
Interesting Personal Questions to Ask
Ask these questions to learn more about their past experiences. “Ask them about their family history and where they come from,” suggests Sanders. “That’s always going to be important.” It can also help provide more context about who they are as a person, reveal insights into what they’re searching for in a relationship, and bring you closer together. Here are some examples: What is your favorite childhood memory? Did you enjoy growing up in your hometown? Where was your favorite place to go on vacation when you were a child? Did you have any favorite family traditions when you were growing up that you want to continue? Were your parents strict, or were they more laid back? What did you appreciate about the way your parents raised you? Is there anything you would do differently if you had kids? Did your parents have a good relationship? What about it do you want to emulate, and what do you want to do differently? Which of your family members gives the best advice? Which of your family members did you look up to the most? Which of your family members were you closest to? Were you closer to one parent than the other? How close-knit was your family when you were growing up? What’s your relationship with your family like currently? Are you happy with it? What do you think is the most valuable lesson your parents ever taught you? What were your favorite subjects in school? What did you love so much about them? Did you have a favorite teacher? Who was your best friend growing up? Are you still friends with them? Did you have a pet growing up? What was your favorite way to spend a Saturday when you were growing up? What was your family’s financial situation like when you were younger? Do you think it affected your relationship with money? Did your family raise you in a certain belief system? Do you think it’s better to have siblings or be an only child? Did you enjoy high school and/or college? Why or why not? Is there a specific life event in your past that you think was a turning point? What happened, and why was it so impactful?
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