Romantic Questions To Ask Your Boyfriend {+To Make Him Laugh}

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Looking for the best Romantic Questions To Ask Your Boyfriend? Sometimes intimacy can be hard.

Finding opportunities to ask questions – even relatively simple questions you just want to know the answers to – can also be hard. However, one great way to break down boundaries in your relationship is to sit down and just ask each other a list of relationship questions, no strings attached.

text reads "romantic questions to ask your boyfriend" with couples laying down, kissing forehead.

Here you’ll find a list of romantic questions to ask your boyfriend to help you grow closer together. Feel free to pick and choose from the list or simply sit down and answer them together.

There’s no better way to increase your intimacy than to sit down and have a long, no-strings-attached talk. Plus, a lot of these questions are really fun, and can only improve your relationship. 

You can always do a relationship check-up to see where you’re both at.

Intimacy in conversation = Romance!

Skip to the bottom if you’re looking for Funny Romantic Questions To Make Him Laugh!

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Romantic Questions to Ask Your Boyfriend: 

  1. What is your favorite memory of our relationship?
  2. What’s something about your life that you’re glad is over?
  3. Tell me about your longest relationship. Why did it end?
  4. What is something you always put off doing? 
  5. Is there a specific taste or food that reminds you of me? 

  1. A specific scent? 
  2. What’s your favorite thing that we do in bed? 
  3. Would you ever want to get married?
  4. Have children? 
  5. How many? Boys or girls? 

  1. What is the first thing you would do if you won the lottery?
  2. What is your favorite thing about me? 
  3. What do you think makes for a happy relationship? 
  4. What is your favorite thing that I do for you? 
  5. Do you believe in fate or destiny or a higher power, or do you believe that fate is determined by our choices?
couple sitting cross-legged on the couch having a conversation.
  1. What movie reminds you of our relationship?
  2. Is there anything that you would consider unforgivable? 
  3. Which of your parents do you have the best relationship with? 
  4. Which one do you think you’re the most like? 
  5. Is there something you’ve always wanted to do, but been too scared to?

  1. Do you think money can buy happiness? Why or why not? 
  2. What would you say is the best thing that has ever happened to you? 
  3. What’s my best physical feature (or your favorite)? 
  4. What’s your dream job, if there were no limitations?
  5. If you could pick any year of your life to do differently or just relive, which would it be and why?

  1. If you could only accomplish one thing before you die, what would you want it to be? 
  2. What’s your biggest pet peeve? 
  3. Do you like being romantic/intimate more in the mornings or at night? 
  4. What are you most proud of? 
  5. If you could pass down one message to your younger self, what would that be? 
couple sitting comfortably on the floor having a conversation.
  1. Do you prefer hugging or kissing?
  2. What would you say is your deepest, darkest fear?
  3. What is something that really makes you feel alive?
  4. When was the moment you knew you wanted to be with me? 
  5. How would you describe your relationship with your family?

  1. Describe your perfect day. 
  2. Do you get jealous when you see me talking to other people?
  3. Describe your relationship with your best friend.
  4. Do you feel like you make decisions primarily based on logic or on emotion?
  5. Do you ever have dreams about me? 
  1. Tell me about some of them. 
  2. What’s your love language?
  3. What do you think we need to work on in our relationship?
  4. Do you consider yourself an introvert or an extrovert? 
  5. If you could change anything about your childhood, what would it be?
  1.  Do you think you want to raise your kids the same way you were raised, or differently?
  2. What would you want to do differently?
  3. How do you like to be treated/taken care of when you’re sick?
  4. Do you hold grudges?
  5. What was your first impression of me? 
couple sitting cross-legged on the couch having a conversation.
  1. What do you love about our relationship?
  2. When did you realize you wanted to kiss me?
  3. What was going through your head?
  4. Do you think it’s possible for a relationship to recover from cheating?
  5. If you could describe our relationship in one word, what word would that be?

  1. What’s your favorite non-sexual activity we do together?
  2. Did you have a role model growing up? Who was it and why?
  3. What did you want to be when you grew up when you were a child?
  4. What’s one way that we complement each other well?
  5. What’s one similarity between us that you love?

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Questions To Ask Your Girlfriend

  1. Is there a sexual fantasy you’ve always wanted to experience?
  2. What about me made you fall in love with me?
  3. What’s your favorite holiday?
  4. What’s your favorite memory associated with a holiday?
  5. What’s the best gift you’ve ever received?

  1. What’s one thing you would like for us to do together that you’ve never experienced?
  2. What’s something I could do for you that would make you really happy?
  3. Where is your favorite place to go on a date?
  4. What is something I do that makes you feel most taken care of?
  5. Do you have a favorite book?

  1. What’s one thing you’ve always been scared to ask me?
  2. Tell me about any pets you had growing up.
  3. What’s your happiest childhood memory?
  4. What’s your favorite part of my personality?
  5. If our relationship suddenly ended, what would you miss the most?
couple laying in bed having a conversation.
  1. What makes you feel better after a long, hard day?
  2. When was your most vulnerable moment?
  3. Where is your favorite place to go on vacation?
  4. What is one secret you’ve always wanted to tell me, but havent?
  5. What’s one thing you always wanted as a kid, but never got? 

  1. What’s your favorite way to give or receive affection? 
  2. What is one thing your parents taught you about relationships?
  3. Did/do you sleep with stuffed animals?
  4. If you could change one thing in our relationship, what would it be? 
  5. What is my best personality trait?

  1. What is one personality trait you want to develop in yourself?
  2. Do you believe in soul mates?
  3. What is one thing you’d like to do with me more?
  4. What is the best gift you have ever received?
  5. Where do you see yourself in 5 years? 10? 20?

  1. What is one thing you would want me to do for you?
  2. Why do you think we are good together?
  3. Do you have anything you want to improve in your life?
  4. Anything you want to improve in our relationship?
  5. What is your ultimate dream date?

  1. Where would you want to go on a honeymoon?
  2. Do you have a bucket list?
  3. What is on your bucket list?
  4. What was your favorite adventure we went on together?
  5. What is the most important thing in life to you?

More Romantic Questions To Ask A Guy

  1. What is your favorite memory of us together?
  2. What do you think is the most romantic thing that has ever happened to you?
  3. What do you love most about me?
  4. What is something that you’ve always wanted to tell me but haven’t yet?
  5. What is your idea of the perfect date?
  6. What is your favorite love song and why?
  7. What is the most important thing that you look for in a relationship?
  8. If you could take me anywhere in the world, where would we go?
  9. What is the most special gift you’ve ever received from someone?
  10. What is one thing that you have always wanted to do for me, but haven’t yet?
  11. If you could relive one moment of our relationship, which one would it be and why?
  12. What is your favorite thing about our relationship?
  13. What is your idea of a perfect romantic evening?
  14. What is the one thing that you admire the most about me?
  15. What do you think is the key to a successful and long-lasting relationship?

Romantic Questions To Ask Your Boyfriend To Make Him Laugh

Humor can be a great way to bond with your partner, and it’s important to have fun and enjoy each other’s company in a relationship.If you want to make your guy laugh while still being romantic, here are some questions you can ask him:

  1. If you could be any romantic comedy movie character, who would you be and why?
  2. What is the most embarrassing romantic moment you’ve ever had?
  3. If you could have a superpower that helps you in your romantic life, what would it be?
  4. If you had to choose between never kissing again or never eating pizza again, which one would you choose?
  5. What’s the cheesiest pickup line you’ve ever used or heard?
  6. If we were to have a movie date night at home, which movie would you choose?
  7. What’s the funniest date you’ve ever been on?
  8. If you could have any animal as a pet to impress me, what would it be?
  9. What’s the silliest thing that makes you feel romantic?
  10. If you could have any celebrity as your wingman, who would it be and why?

  1. If you could have a romantic dinner with any historical figure, who would it be and why?
  2. What’s the most ridiculous thing you’ve ever done to impress a crush?
  3. What’s the weirdest romantic dream you’ve ever had?
  4. If you were to write a romantic comedy movie about our relationship, what would the plot be?
  5. What’s the funniest thing you’ve ever said to try and impress someone you were interested in?
  6. If you were a love song, which one would you be and why?
  7. What’s the most awkward romantic situation you’ve ever been in?
  8. If we were stranded on a deserted island, what romantic item would you want to have with us?
  9. What’s the most cringe-worthy romantic gesture you’ve ever seen in a movie?
  10. If you could take me on a romantic trip to any fictional place, where would it be and why?

  1. What’s the funniest romantic story you’ve ever heard?
  2. What’s the most ridiculous romantic outfit you’ve ever worn or seen someone wear?
  3. If you were to write a love letter to your favorite food, what would it say?
  4. What’s the most absurd romantic stereotype that you’ve ever heard?
  5. If you could switch places with any romantic comedy character for a day, who would it be and why?
  6. What’s the most hilarious romantic prank you’ve ever pulled or seen someone else pull?
  7. If you had to choose between being a romantic lead in a movie or being a superhero, which one would you choose?
  8. What’s the most cringe-worthy romantic song you secretly enjoy?
  9. What’s the most ridiculous romantic line from a movie that you’ve ever heard?
  10. What’s the most unexpected thing that’s ever made you feel romantic?

Create Your Own Romantic Questions For Your Boyfriend

Take an afternoon together to ask each other some of these intimate questions, or simply ask one or two as conversation starters now and again to start off a conversation and let it flow naturally. Some of the best conversations come from your own creative ideas generated from others. 

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

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