Yes, your boyfriend has a past. And it’s probably a lot more interesting than you think. If you want to get to know him better – and who doesn’t? – you need to ask the right questions.
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Here are over 100 questions to help get the conversation started. From serious questions about your relationship to fun and quirky questions that will have you both laughing, we’ve got you covered.
So, read on and get ready to learn more about your partner!
Fun Questions to Ask Your Boyfriend
When you’re building a connection with your partner, questions can be an easy way of tapping into his thoughts and emotions to better understand him or simply have some fun together.
Whether you’re looking to kill some time on a road trip or you just want to get to know him better, these questions will do the trick!
- If you could be anyone in the world for a day, who would it be? Why?
- What’s one thing you wish people did more often?
- If you could pick one place you’ve always wanted to visit, where would it be and why?
- Who is your favorite Disney princess, and why?
- Do you believe in aliens or UFOs?
- If given the opportunity, would you visit another planet/galaxy?
- If you could relive any moment in your life, what would it be and why?
- Are there any moments throughout history that have stood out to you as especially significant/important for humankind?
- What’s one thing about yourself that has changed over the years since childhood/teenage years/college/etc.?
- If you won the lottery tomorrow, what would you do?
- What’s something you’ve always wanted to try but haven’t gotten around to?
- What was one of the most ridiculous things you tried as a kid?
- If there was a button that could erase one day of your life, would you press it?
- If you could choose to be a cat or a dog – which would it be and why?
- Would you rather live in an igloo in Alaska or a tent in Africa?
- Would you rather have the ability to fly or be invisible?
- If a genie popped out of my phone right now and said she’ll grant you 3 wishes, what would they be?
- Where do you see yourself living in five years?
- If you could travel anywhere tomorrow, where would you go?
- If you could live in any decade, which would it be?
- Who is your favorite actor/actress?
- What is your dream house like?
- Would you like to be famous? Why or why not?
- If you could have dinner with anyone in the world, who would it be?
- If you could bring back one deceased person for one day, who would it be, and what would you do with them?
- What music artist is your guilty pleasure?
- Are there any unsolved mysteries that interest you?
- Do you believe in ghosts/the supernatural?
Cute Questions to Ask Your Boyfriend
If you want to keep your relationship fresh, it’s a good idea to ask your boyfriend some cute questions from time to time. This will help you get to know him better and keep the conversation flowing.
- What was the last book you read?
- Would you rather have superhuman strength or the ability to read people’s thoughts?
- When did you meet your best friend, and how did it happen?
- If you could visit any location in history, where would it be?
- What was the last dream you remember having?
- Who is/was your favorite teacher? Why?
- What are some things on your bucket list?
- If money wasn’t an issue, what would be your dream job?
- What is one thing you would change about your life if you could?
- What are the things that make you really happy in life?
- What are some of your favorite memories from childhood, and why do they mean so much to you?
- What are some of your pet peeves?
- If you could be the fictional character of your choice, who would you choose to be?
- Who’s your favorite comedian or movie director?
- What’s the most embarrassing moment of your life?
- What’s something you’re scared of now that you weren’t before?
- If you could be any animal, what would it be and why?
- What’s your favorite type of sandwich in the world and why?
- What is your favorite memory of us together?
- If you could have any superpower, what would it be?
Sexual Questions to Ask Your Boyfriend
If you want to keep the spark alive in your relationship, it’s important to keep the bedroom fun and exciting. Whether you’re curious or want to try new things in your sexual life, these dirty questions to ask your boyfriend will give you the answers you need! Here are a few sexual or freaky questions to ask your boyfriend to help get things started.
- Have you ever had phone sex?
- Do you have any embarrassing sex stories?
- What was the weirdest thing you’ve ever done in bed?
- Have you ever had sex in public?
- If you could have sex with every celebrity in the world, who would it be?
- What position do you like the most? What position do you like the least?
- What is one thing you would like to try in bed?
- What do you do if your partner is not in the mood?
- What is your favorite way to masturbate?
- What are some sex positions to try out?
- What fantasies would you like to explore?
- What kind of sex toys have you used?
- What turns you off the most in bed?
- Is there anything you would never do in bed?
- What scares you most about being naked with your partner?
- How long can you go without having sex?
- Have you ever had anal sex?
- Have you ever had an orgy?
- What kind of sexual activities interest you?
- What are your thoughts on porn?
- Do you like to keep things spicy in the bedroom, or do you prefer to stick to one routine?
- Do you have any fantasies you’d like to try out with me?
- Have you ever had a threesome and, if so, would you want to do it again?
- Would you be comfortable with me masturbating in front of you or vice versa?
- Do you like to be submissive or dominant in bed?
- Would you ever want to try bondage or roleplaying?
- Are there any specific things that you would like to do together sexually?
Personal Questions to Ask Your Boyfriend
You’ve been dating for a while now, and you think it might be time to get to know your partner better. But where do you start? What questions should you ask?
There are no bad questions when it comes to getting to know someone, so here are some queries that will help deepen your understanding of the person sitting across from you at dinner or in bed.
- How would you define love?
- What are deal breakers for you in a relationship?
- When was the last time you cried in front of someone?
- What were some memorable moments in your life so far?
- Who do you admire most and why?
- If you found out that there are only two months left to live, what would be the top things you want to do before then?
- Is it possible to be friends with an ex after a breakup?
- What was the happiest moment of your life?
- Do you believe in love at first sight?
- What are your thoughts on religion/spirituality?
- How important is money to you?
- What are your fears and insecurities?
- What are your passions in life?
- What do you think is the most important thing in a relationship?
- What is the most meaningful gift you’ve ever received?
- What’s the most interesting place you’ve been to?
- Would you prefer a small or big wedding and why?
- What things about yourself make you happy/proud of yourself?
- What are your thoughts on religion?
- What scares or worries you the most about relationships/marriage?
Romantic Questions to Ask Your Boyfriend
If you are looking for ways to deepen your relationship with your boyfriend, you might ask him some romantic questions. By doing so, you can learn more about what he loves and values in a relationship and gain insight into his thoughts and feelings about love and romance.
Asking your boyfriend romantic questions can help keep the spark alive by providing new topics of conversation. If you are ready to take your relationship to the next level, try asking your boyfriend some of these romantic questions.
- Do you believe in soulmates and love at first sight?
- When did you know I was the one for you?
- What is your idea of the perfect date?
- What are your thoughts on love and relationships?
- Do you believe in soulmates?
- Do you have any secret fantasies about us or our relationship?
- Are there any special places where you would like to take me on a date?
- How would you describe yourself as a lover?
- When do you feel most romantic?
- What are your thoughts on love?
- What are your favorite romantic movies?
- What are your favorite romantic songs?
- What does romance mean to you?
- When do you feel most romantic?
- What is the most romantic thing you have ever done?
- What is your favorite romantic scent?
- What is love to you, and what are some of the best aspects of being in a committed relationship?
Friendship Questions to Ask Your Boyfriend
Friends are some of the most important people in our lives. They are the people we can always count on for helping us out when someone has wronged us or to laugh with on the bad days.
Asking him questions about his friends will not only tell you more about him but will also deepen your connection.
- How did you and your friends meet?
- What is the best thing about your friends?
- What is the worst thing about your friends?
- Who is the wildest friend you have?
- Who is the most responsible friend you have?
- What do you and your friends do for fun?
- Are you hanging out with your friends as much as you used to now that we’re dating?
- What is the most meaningful thing a friend has ever done for you?
- What is the biggest challenge you’ve faced with friendships?
- Who are your closest friends?
- What do you and your best friend do together?
- What games do you like to play with your friends?
- Who are the people you spend most of your time with?
- When was the last time that a friend told you they loved you?
- Which friend is the most like you?
- How do you define friendship?
Questions to Ask Your Boyfriend About His Past
If you want to get to know your boyfriend better, it is important to ask him questions about his past. When you date someone, it’s easy to focus on the future, but by asking your boyfriend about his history, you will learn a lot about who he is and see how various aspects of his life have shaped him into the guy he is today.
- What was your favorite toy as a child?
- What were some things you liked to do for fun when you were younger?
- What was the most memorable moment from your childhood?
- Do you have any siblings, and if so, what is the most interesting thing about them?
- Who was your best friend when you were growing up?
- What were some of your favorite childhood memories?
- What did you want to be when you grew up?
- How did you meet your first girlfriend?
- What was the most serious relationship you’ve been in?
- How do you think your upbringing has affected the way you view relationships?
- What do you remember most about your first kiss?
- How many relationships have you been in?
- What did you learn from your past relationships?
- What was the most meaningful relationship you’ve been in?
- How would you describe yourself as a child?
- What were some things you liked to do for fun when you were little?
- Where did you grow up, and what was it like there?
Family Questions to Ask Your Boyfriend
Family is an important part of life, and you will probably develop a closer relationship with your boyfriend’s family than with his friends. When dating someone new, it is reasonable to be curious about their background, including who they are close to, to understand what kind of person they are or would like to be.
- What is your relationship with your parents like?
- Are there any family traditions that are important to you?
- Do you come from a close-knit family?
- Who is your favorite family member?
- Do you ever get homesick when you’re away from your family?
- Who is the most intelligent person in your family?
- Who is the black sheep of the family?
- What is the craziest thing one of your family members has ever done?
- How do you think your upbringing has shaped who you are today?
- How often do you get to see your family, and how long has it been since you last did?
- Do you have any family heirlooms? If so, what are they, and what makes them special?
- Who are some of your favorite family members to spend time with?
- Do you have any funny family stories?
- How does your family celebrate holidays?
- What are your favorite memories of holidays with the family?
- How much input does your family have on significant decisions in your life?
Intimacy Questions to Ask Your Boyfriend
Love is a beautiful thing. It is something that every couple strives to maintain in their relationship, and it requires work from both sides. One way to do this is by having good communication with your partner, including asking questions and talking about what you want out of the relationship.
- What is your definition of intimacy?
- What are your thoughts on open relationships?
- What is your definition of cheating?
- Have you ever been in a serious relationship before?
- How often do you think we should have sex?
- What are your favorite ways to have intimate moments with me?
- How can I be more supportive of you?
- Do you think we spend enough time together?
- Which activities do you prefer for building intimacy or sharing affection with me?
- What would make our sex life better for both of us in terms of intimacy, romance, and physical contact (not just intercourse)?
- Are there any aspects of our intimacy that you would like to change?
- What is your idea of the perfect date night?
- What makes you feel close to me?
- How can we be more intimate in our everyday life?
- Where are good places we could go on a date for an intimate night out?
- What’s the most intimate moment we’ve shared so far?
- How did your last relationship end, and why do you think it didn’t work out?
- How long do you think a person needs to know someone before becoming intimate with them?
- What is your biggest fear in a relationship, and why does it scare you so much?
- Where or from whom did you learn about sex the most growing up?
Relationship Communication: Questions Create Deeper Intimacy
The questions in this article will help you get to know your boyfriend better and understand who he is as a person. He may be more willing to share his thoughts and feelings with you if you ask him about what makes him happy or sad, how he views relationships, or even the family dynamics of his upbringing.
These essential things can affect how well your relationship grows into something meaningful and lasting. By developing this kind of healthy and open communication, you will both feel more comfortable with each other and work through any problems that may come up.