Get to Know Your Boyfriend Better With These 105 Questions


    You may think you know everything about your boyfriend, but spoiler alert: you probably don’t. No matter how long you’ve been together, it’s almost impossible to know everything about your partner at any given time. But the more you understand about your BF, the stronger your relationship will be.

    Asking your boyfriend the right questions is especially important if your relationship is relatively new. If you’re looking for this person to become a life partner, you want to know if you’re compatible. You don’t want to move in, or get engaged—or both—only to learn that your boyfriend doesn’t want to have kids when you really do. These are things you should discuss before getting serious; otherwise, you might be doomed for disappointment down the line.

    We’ve compiled a long list of questions to ask your boyfriend to get to know him better and to see if you’re on the same page about your relationship. You’ll likely know the answer to a number of these questions, but it’s also good to hear what your boyfriend thinks about himself. Who knows? You may think you know something about your man, but it turns out what you thought was wrong.

    You’ll notice that some of these questions are personal, and a few are uncomfortable to address. We’re very well aware, but that’s in part why you need to ask these questions and answer them truthfully.

    So, here are 105 questions to ask your boyfriend. We’ve broken them down by category: relationship compatibility, sex, and fun.

    Questions About Relationship Compatibility

      • Do you want to have kids?
      • Would you consider adopting children?
      • Are you okay with having a surrogate?
      • How close are you to your family?
      • Is it important to live close to your family?
      • How long was your longest relationship?
      • Why have your past relationships ended?
      • Have you ever lived with a partner? What was that like?
      • Are you religious or spiritual? How important are religion and spirituality to you?
      • How many hours a week do you typically work?
      • How many hours a night do you sleep?
      • How important is it to you to have a lot of money?
      • What’s an accomplishment you’re most proud of?
      • When was the last time you voted?
      • Who did you vote for?
      • What’s the number one thing you look for in a partner?
      • Are you on time? How important is it that your partner runs on time?
      • What is something important you’ve learned from another couple?
      • What is your love language?
      • What do you fear most in a relationship?
      • What do you think is the most essential element for maintaining a relationship?
      • Are you friends with your exes?
      • Are you more introverted or extroverted?
      • Do you hold onto grudges?
      • What makes you irrationally angry?
      • Have you struggled with mental illness?
      • How often do you clean your apartment?
      • Do you make your bed every day?
      • How long do you tend to leave dishes in the sink?
      • If one of us was to make more in the relationship, how do you feel about splitting things?
      • When can you tell you’re really comfortable with a partner?
      • Have you ever been in an abusive relationship?
      • What do you consider cheating? (Is sending nudes to someone on Instagram cheating? Is a kiss on the lips cheating, etc.?)
      • Have you ever been cheated on?
      • Have you ever cheated on your past partners? Did you tell them?
      • Do you think a relationship can come back from cheating?
      • Is your ideal relationship monogamous, open, polyamorous, or another form of ethical non-monogamy?
      • Have you ever had your heart broken?
      • Have you ever struggled with addiction?
      • What makes you jealous?
      • How do you handle your jealousy?
      • What’s the biggest misconception people have about you?
      • Are you in therapy? (If so, for how long? If not, why not?)
      • Have you ever snooped on a partner?
      • How often do you see your friends? How important are your friends to you?
      • Do you love to travel?
      • What do you like to do on the weekends?
      • Are you more of a homebody, or do you like to go out and party?
      • Do you like to dance?
      • Do you drink, smoke, or do drugs? How often? What’s your relationship like with substances?
      • Do you like to read? What type of books?
      • When, if ever, do you think it’s okay to lie?
      • Do you like to watch TV? What genre of TV?
      • What do you think is your best attribute as a boyfriend?
      • If I called up all your exes, what would be the other thing they all say you have in common?
      • What makes you the most emotional?
      • What brings you the most joy?
      • What’s the biggest risk you’ve taken?
      • What do you like most about yourself?
      • What do you like the least about yourself?
      • Do you cry? How often?
      • Would you ever want to have pets? Cats, dogs, another pet?
      • Could you ever see yourself in a long-distance marriage?
      • How do you feel about hiring a nanny, housekeeper, etc.?
      • What did you learn about yourself during covid?
      • If you could snap your fingers and change one thing about your life, what would it be?
        gay couple eating lunch at home

        Claudia BurlottiGetty Images

        Questions About Sex

        • How often do you like to have sex in a relationship?
        • What do you like to do sexually?
        • Do you have any kinks/fetishes?
        • How open are you to exploring new things in the bedroom?
        • Do you like using sex toys? Which toys are your favorite?
        • Do you think you’d ever be open to having a threesome?
        • Do you like role play? Which scenarios?
        • Have you ever done any BDSM? What was your role—the dominant or submissive?
        • Would you feel comfortable telling me if our sex was growing stale? How would you tell me?
        • Thoughts on anal sex?
        • Are there any sexual things that you’re ashamed of? Why?
        • Are you into or would you be down to try prostate stimulation?
        • How often do you watch porn when in a relationship?
        • Do you like (or would you be open to) watching porn with a partner?
        • Would you ever be interested in going to a sex club together?

          Questions That Are Fun and Silly

          • Who was your childhood celebrity crush?
          • Share one of the times you laughed the hardest.
          • If you could only listen to one song for the rest of your life, what song would it be?
          • What word do you hate?
          • Which celebrities have you met? What were they like?
          • What is your favorite guilty pleasure to watch or read?
          • What’s the wildest thing you’ve ever done on a dare?
          • What were you like in high school?
          • Which actor would play you in a movie about your life?
          • What is your favorite part about being an adult?
          • What’s the weirdest thing you’ve ever bought?
          • What’s one of the most embarrassing things that has ever happened to you?
          • Have you ever been to a palm reader?
          • Do you believe in ghosts?
          • Have you ever broken any bones?
          • Do you collect anything?
          • What would be your “at bat” song?
          • Do you believe in any superstitions?
          • If you could go back to one moment in your life and do things differently, which moment would you choose? How would you do it differently?
          • Have you ever been skydiving?
          • Have you ever tried to invent something?
          • Have you ever been scuba diving?
          • Would you ever go on a silent retreat?
          • If you could change your name to anything, what would you pick?

            Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, culture, and entertainment.

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