180+ Deep Questions to Ask Your Boyfriend (& How to Ask Them) (2024)

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Get to know each other better with these intimate conversation starters

Co-authored byCourtney Quinlanand Cheyenne Main

Last Updated: February 16, 2024Fact Checked

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  • Deep Questions to Ask Your Boyfriend
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  • Bringing up Deep Questions
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Whether you’ve been together a few weeks or ten years, asking your boyfriend deep questions can enhance your communication, create opportunities for vulnerability, and strengthen your connection. Asking about your boyfriend’s hopes, fears, dreams, emotions, and past experiences can encourage him to share his thoughts, allowing you to learn more about him and share meaningful discussions. We compiled a list of the best questions to ask your boyfriend to get to know him on a deeper level. Read on for more!

Section 1 of 2:

Deep Questions to Ask Your Boyfriend

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  1. 1

    Explore your boyfriend’s emotions with these personal questions. It can be difficult to share your private thoughts and feelings, especially when you haven’t ventured into that territory before. Try to nod and give verbal assurances to your boyfriend when he answers, and answer the question yourself to prevent him from feeling singled out.[1]

    • What is something you’ve always wanted to learn or try?
    • What’s something you’ve learned by observing the person you like least?
    • When did you last cry in front of another person? By yourself?
    • What is your favorite way to practice self-care?
    • What is the most challenging experience you’ve had in life?
    • When do you feel most fulfilled?
    • Do you ever find yourself worrying about the things you have no control over?
    • What's a question you wish more people asked you?
    • What is the most meaningful compliment you’ve ever received?
    • If you could be anywhere in the world right this moment, where would you be and what would you be doing?
    • What makes you happy?
    • What would your perfect day look like?
    • How do you handle stress or difficult situations?
    • When you look in the mirror, do you like what you see?
    • What’s something that’s missing in your life?
    • What do you consider to be your biggest personal achievement? Why?
    • How do you cope with failure or setbacks?
    • How have you grown as a person in the past year?
    • What did you do to pull out of the darkest time in your life?
    • What are some unfulfilled things in your life right now?
  2. 2

    Ask him about his romantic past and what he thinks about relationships. Learning about what your boyfriend values in relationships is incredibly important, especially if you’re planning to be together long-term. Even though it may be uncomfortable, asking about his past relationships may help you understand how his identity and views were shaped by those experiences.[2]

    • What is your love language?
    • Do you envision yourself having kids?
    • Do you think it's possible to stay in the honeymoon phase forever?
    • Why do you think people cheat?
    • Of the people we know, whose relationship do you admire most and why?
    • Do you see yourself getting married one day?
    • Would you ever be in an open relationship? Why or why not?
    • Why did your last relationship end?
    • Do you still keep in touch with your exes?
    • What drains you in relationships?
    • Do you think a relationship can come back from cheating?
    • How would you describe a happy relationship?
    • Have you ever had your heart broken?
    • Would you sacrifice your career goals for love?
    • Have you ever broken up with someone? How’d you do it?
    • How do you define trust in a relationship?
    • How do you know when you’re really comfortable with someone?


  3. 3

    Ask your boyfriend how he thinks your relationship is going. Emotional intimacy is all about revealing your true self to your partner and using that trust and authenticity to keep the relationship going. Try to ask your partner how he feels about your relationship currently and address any issues that might be present to make your relationship stronger.[3]

    • What did you think when you first saw me?
    • What is your biggest fear or concern about our relationship?
    • What would you like us to do more of in our relationship?
    • How do you want to see our relationship evolve in the next year?
    • What is an aspect of my personality that you don’t love but have been willing to accept because you love me?
    • Do I have any financial habits that bother you?
    • What do I do that makes you feel most safe and loved?
    • How will we know that our relationship is working?
    • Are there any patterns that popped up in your past relationships that you see happening with us?
    • What are some of your favorite memories we’ve made?
    • How do we let each other know when we need space?
    • What is your favorite way to spend quality time together?
    • How do you envision our future together?
    • Is there anything that I can do to communicate better when we have a conflict?
    • What is something you appreciate about our relationship, and why?
    • What's something we could change about our relationship to make it stronger?
    • Do you feel like there are gender or societal pressures in our relationship?
    • How can we better support each other in our individual goals?
  4. 4

    Talk with your boyfriend about your needs and desires in the bedroom. Research shows that when couples talk about sex, they have more satisfying sex lives.[4] Sometimes talking about sex can be more vulnerable than what happens in the bedroom, so try to start the conversation by talking about what’s going well first, then delve into the deeper questions.

    • What’s the best sex we’ve ever had?
    • Would you like me to be more or less assertive in the bedroom?
    • Do you like it when I make the first move?
    • Has sex ever complicated your past relationships? How?
    • During sex, do you prefer having the lights on or off?
    • Have you ever had any sexual experiences that made you feel uncomfortable? Are there any triggers we should be aware of?
    • Are there any unmet needs or desires you have in our sexual relationship?
    • How do you view the connection between emotional intimacy and sexual intimacy?
    • What's a fantasy of yours we've never talked about?
    • Did your childhood impact what you thought of physical intimacy as you grew up? How?
    • What’s one public place you would like to have sex in?
    • Are you a fan of PDA? Why or why not?
    • How many times do you think couples should have sex a week?
    • How do you feel about trying new sexual experiences or experimenting with different techniques?
    • What are your beliefs and values regarding sexual intimacy, and how do you see them fitting into our relationship?
    • Are there any specific sexual acts or positions that you particularly enjoy?
    • Do you wish I was more affectionate?
    • Do you have any preferences or expectations about initiating sex? What are they?
    • Have you ever had a one-night stand? How was it?
    • How do you feel about incorporating sex toys into our time in the bedroom?
    • What is your opinion on dirty talk? Do you love it or hate it?
  5. 5

    Ask your boyfriend about his childhood and family. Matchmaker and dating coach Lauren Sanders says one of the best ways to get to know your partner better is to “ask them about their family history and where they come from.” What his childhood was like can tell you a lot about how he might act or make decisions if you get married, move in together, or have kids.

    • What did you like the most about where you grew up? What did you like the least?
    • What was your family’s financial situation like growing up, and how has it impacted your relationship with money?
    • Would you change anything about your upbringing?
    • What is your favorite childhood memory, and why?
    • What’s the silliest or weirdest nickname you’ve ever been given by your family, and why?
    • What is your favorite childhood TV show or cartoon?
    • What’s your relationship like with your parents?
    • What have you learned from your family that has helped you personally or professionally?
    • What do you wish you had more of growing up?
    • What is your favorite childhood holiday or tradition?
    • Does your family have any cultural values or traditions I should know about?
    • What's the story behind your middle name?
    • How has your family background influenced your beliefs or values?
    • Who are you closest to in your family?
    • Besides your parents, who shaped you the most during your childhood and teens?
    • What is your biggest fear or concern when starting a family?
    • What’s the first time you saw your parents cry?
    • How do you envision your future family, and what kind of parent do you think you would be?
    • What was your favorite subject in school? What subject were you best at?
    • What were your first words as a child?
  6. 6

    Talk with him about his values and any long-held personal beliefs. Building emotional intimacy with your boyfriend means diving into questions that explore what values and ideas factor into how they see the world.[5] Try to ask him about his hot takes, political opinions, relationship with religion, and what he thinks about social issues or society in general.

    • What social or political issues are most important to you, and why?
    • What’s your most controversial opinion?
    • Could you date someone who does drugs?
    • What is your favorite way to give back to your community?
    • How important is spirituality or religion to you?
    • What are some beliefs you grew up with but don’t subscribe to anymore? Why?
    • Where are you finding the most meaning in life?
    • Do you think it's ever okay to lie? In what circ*mstances?
    • What’s something you’re afraid to lose?
    • What do you strongly believe in, even if it goes against societal norms?
    • What’s your relationship with money? How does that impact your spending habits?
    • If your loved ones didn’t approve of me, what would you do?
    • Have you ever been given an opportunity you didn’t think you deserved? What was it?
    • Do you feel like race has affected your life? How so?
    • What is one principle you hold that you would never compromise on?
    • Do you believe in a higher power? Why or why not?
    • Do you have any regrets? If you could go back in time, would you do things differently?
    • What’s something that people do that gets on your nerves?
  7. 7

    Talk about your career goals and life ambitions together. Matchmaker and dating coach Courtney Quinlan recommends “asking [him] about [his] future goals in life.” To promote good communication, she says that it’s important to talk “about where you stand,” “where you see things in the future,” and how you can “[work] together to make those dreams come true.”

    • What is your biggest career ambition, and how do you plan to get there?
    • How do you handle balancing work and personal life?
    • What do you wish you could do but feel like you don’t have the time or resources?
    • What’s a job you would hate doing?
    • What is your favorite way to explore and experience new things?
    • What is your proudest accomplishment in life so far?
    • What’s stressing you out the most this week?
    • What is one thing you could do differently to get closer to achieving your goals?
    • Where do you see yourself in five years?
    • How do you define success?
    • What is the one thing you want to be remembered for?
    • What is something you would like to accomplish in the next year?
    • If you were able to work in any other job for a year, what would it be?
    • Do you have any routines that you stick to religiously?
    • If you died now, would you have any regrets?
    • What motivates you to work hard?
    • What do you want to do when you retire?
    • If you didn’t have to work to live, what would you do with your time?
    • What gets you out of bed in the morning?
    • Would you rather win the lottery or work at the perfect job? Why?
    • How do you envision your ideal future?
  8. 8

    Try out one of these thought-provoking philosophical questions. These questions don’t necessarily have right or wrong answers but are just meant to challenge you and your partner to think about life differently. If the two of you have different values and beliefs, these questions might help you discuss them on a deeper level.

    • Do you think there’s a better alternative to our political/economic system?
    • Do you think humans are inherently good or inherently evil?
    • Can artificial intelligence be creative?
    • If everyone spoke their mind, do you think this world would be a better place?
    • Do you think we have free will?
    • Why do you think there is so much suffering in the world?
    • Do you think organized religion will have a bigger or smaller place in society in the future?
    • Do you think people could ever truly change? Why or why not?
    • What do you think is the most pertinent issue our country is facing today?
    • What would you change about our current political system?
    • What do you think happens after death?
    • What is your stance on controversial topics like abortion or the death penalty?
    • If you were President, what would be the first change you would make?
    • What is the meaning of happiness?
    • How do you feel about religion?
    • What from the past is worth preserving?
    • If the world ended tomorrow, what would you do on your last day?
    • Do you think aliens exist?
    • Do you think our society is progressing or regressing?
    • Do you believe in soul mates? Why or why not?
    • What's more important—science or art?
    • Do you think fate exists?
  9. 9

    End your deep conversation with these fun, light questions. If you and your boyfriend made it all the way to the bottom of this list, celebrate your dive into deeper conversation and lighten the mood a little bit with a few of these silly questions. When you run out, try these funny and random questions next!

    • What's your favorite conspiracy theory?
    • Which one of these objects reminds you most of me: An umbrella, a light bulb, a tree, a loaf of bread, or a pen. Why?
    • If you were visited by aliens, where would you take them to explain our culture?
    • What’s your favorite pasta shape?
    • Would you still love me if I was a worm?
    • If you could be any animal, what animal would you be?
    • If you could have a personal theme song that played whenever you entered a room, what song would it be?
    • If you could have dinner with any celebrity, dead or alive, who would it be? What would you ask them?
    • What would an amusem*nt park designed specifically to make you happy be like?
    • If you could have any animal as a pet, what would you choose?
    • What fictional character do you most identify with?
    • Do you prefer to sleep in or wake up early on the weekends?
    • If you could take your future kids to their first concert, who would you take them to see?
    • If you were a superhero, what would your superpower be and why?
    • If you won the lottery, where would you travel and why?
    • What’s the worst first date you’ve ever had?
    • Have you ever done anything illegal?
    • If we were to compete in a reality show together, which would you choose?
    • What was your best Halloween costume? Show me a picture if you have one.
    • What’s a movie you can watch over and over again?
    • What role would you play in the group of people trying to survive a zombie apocalypse?
    • Would you rather be able to read people’s minds or travel anywhere in the world with the snap of a finger?
    • What do you want to do in retirement?
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Section 2 of 2:

Bringing up Deep Questions

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  1. 1

    Set aside time when you’re both free, like during a night out. Try not to spring these conversations on your boyfriend when he’s about to go somewhere or as soon as he gets back from work. Instead, try to integrate deep questions into a conversation you’re already having when you’re on a date or just sitting on the couch together.[6]

    • Ideally, wait until you’re in a quiet place where you can both talk uninterrupted to ask these deep questions.
    • You can also create a routine where you and your partner pick a few questions off the list during dinner or every night you’re doing something together.
  2. 2

    Try to use a gentle tone and practice active listening as he talks. If you’re creating your own deep question, make it open-ended and try to phrase it as non-judgmentally as you can. If he gives you a short answer, you could ask, “Why do you feel like that?” or “What was that like for you?”[7]

    • As your boyfriend talks, try to make eye contact, nod your head, and lean slightly forward. You can also try a few verbal encouragements like “Really?” or “Mmhmm.”[8]
    • After he finishes talking, repeat what he said to make sure you understand and ask questions if you’re trying to understand the main point of his statement.[9]
  3. 3

    Answer the question after your boyfriend does to deepen your bond. Opening up to others isn’t always easy, and answering the same question you ask can make both people feel seen and heard. It can also help prevent the questions from feeling one-sided and create more opportunities to be vulnerable with each other.[10]

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      Expert Interview

      Thanks for reading our article! If you’d like to learn more about relationships, check out our in-depth interview with Courtney Quinlan.


      1. https://www.mindbodygreen.com/articles/how-to-get-someone-to-open-up
      2. https://www.psychologytoday.com/us/blog/fulfillment-at-any-age/202307/what-you-can-learn-about-yourself-from-your-past-lovers
      3. https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner#why-deep-questions
      4. https://www.gottman.com/blog/how-to-feel-comfortable-expressing-sexual-desires-with-your-partner/
      5. https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner
      6. https://www.lovetoknow.com/life/relationships/intimate-questions-ask-your-partner
      7. https://psychcentral.com/relationships/trust-and-vulnerability-in-relationships
      8. https://psychcentral.com/lib/become-a-better-listener-active-listening
      9. https://www.psychologytoday.com/us/blog/in-it-together/202006/active-listening-skills

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      About This Article

      180+ Deep Questions to Ask Your Boyfriend (& How to Ask Them) (32)

      Co-authored by:

      Courtney Quinlan

      Matchmaker & Dating Coach

      This article was co-authored by Courtney Quinlan and by wikiHow staff writer, Cheyenne Main. Courtney Quinlan is a Matchmaker and Dating Coach and the Owner of Midwest Matchmaking. With over 15 years of experience, she specializes in finding individuals a compatible partner, providing guidance throughout the dating process, and crafting events for singles in the Midwest. Courtney holds a BS in Broadcast Journalism from The University of Nebraska at Omaha.

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      Co-authors: 3

      Updated: February 16, 2024


      Categories: Relationships

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