101 Romantic And Deep Questions To Ask Your Boyfriend

Get curious, explore, and connect without holding back anything on your mind.

Reviewed by Dr Nancy B Irwin, PsyD
By Harini Natarajan, Certified Emotional Intelligence Practitioner

A lasting connection is built on knowing your loved one intimately. The best way to build this bond is to have lots of fun questions to ask your boyfriend. Find out what your partner has in their heart by exploring their interests. Getting into a meaningful conversation with your partner is essential to building a deep and fulfilling relationship. If you aren’t sure where to start, we’ve got you covered.

Today is the day to take your romance to the next level, so set the tone for your romantic rendezvous. In this article, you will learn all the questions you want to ask your partner and the ones you didn’t know you should. We have listed 101 questions covering a wide range of topics. Make sure to pick the ones that apply to your partner and take time to get to know each other, both physically and figuratively! Be sure to have fun while you do it!

101 Questions To Ask Your Boyfriend For Fun

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  1. How often have you got up to go into a room, then stood at the doorway because you forgot why you wanted to go into the room?
  1. How often does your brain put itself on autopilot? Are you aware of it when it happens?
  1. What names would you never give your own child? Name at least three.
  1. What is the most relaxing thing you can get done or do for less than 500 rupees?
  1. What is the most puke-worthy drink you have consumed? Where did it happen?
  1. How do you waste your time? What are your guilty pleasures?
  1. What silly things are you capable of doing that you take a lot of pride in?
  1. If animals were as intelligent as humans, which animal would you hire as your secretary? What would you name it?
  1. Do you think fish have necks? Explain. Can you draw a picture of a fish with a neck for me?
  1. Who has been your strangest celebrity crush that others don’t like but you have a soft corner for? Why do you like him/her?
  1. If you were a fruit, which one would you be and why?
  1. What has been the strangest conversation you have ever overheard? Do you remember the details?
  1. What kind of chocolate would you use to build your dream mansion?
  1. What would you do if a guy was interested in you and asked for your number?
  1. If you were ice cream, which flavor would you be? Which flavor would you absolutely loathe to be?

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  1. What is the story behind your latest Insta/ Facebook photo? Who took the picture?
  1. Describe the worst first date you have ever been on. Why was it so awful?
  1. If you could be any superhero, who would you choose? Why?
  1. What crazy things would you do (and try to get away with) if you were stinking rich?
  1. What was the last thing you Googled? Is your browser history SFW (safe for work)?
  1. Did you ever receive a weird wrong number text or call? What did they say?
  1. If you could name yourself, what would be the coolest name you would choose?
  1. If you were a girl, would you date Batman or Superman? Why?
  1. Has someone ever confessed their secrets to you while being drunk? What did they say?
  1. If someone you hate had something on their face, would you tell them?
  1. What is that one thing that you have never told anyone because you were embarrassed?
  1. Do you believe in ghosts? If yes, have you ever seen one?
  1. Is there anyone you are afraid of? Why?
  1. Who is your favorite sibling?
  1. What would you rather have – respect or unlimited money?

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  1. Who among your friends are your favorites? Who do you like to spend time with the most?
  1. What was your favorite toy as a child? What is your favorite toy now? 😉
  1. Did you ever have a crush on anyone I know?
  1. If you were forced to leave your house at a moment’s notice, what is the one thing you would grab to take with you?
  1. Name the TV shows you could binge watch all day. Which one is your favorite?
  1. What quirks does your body have? Are you embarrassed of them?
  1. Which parent is your favorite? Why?
  1. Do you think I look sexy in glasses? Do you think I should try a different style?
  1. What have you always been a snob about? Do your friends give you grief about it?
  1. Do you procrastinate? Explain.
  1. Do you judge people too quickly? How often are you right about your judgment?
  1. You just found two thousand rupees on the ground. What would you do?
  1. If drugs were legal, would you try them?
  1. What are some traits you like about yourself?
  1. If you could change three things about your life, what would they be?

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  1. What are the three things that you wouldn’t change about your life, no matter what?
  1. What is your favorite drink and why?
  1. If you were forced to eat the same food for a month, what would you choose?
  1. Where would you choose to live if work and money were not a factor?
  1. Do you listen to your mind or heart when making important decisions?
  1. What is the worst yet most expensive purchase you have ever made?
  1. Who was your role model as a kid? Why did you like him/her?
  1. What is the best piece of advice you have ever received? Who gave it to you?
  1. What is your biggest pet peeve?
  1. If your life was a movie, what would you name it?
  1. What is that one thing on your bucket list you freak out about and keep pushing back?
  1. If money was not a factor, would you leave your job and travel the world? Where would you go?
  1. If you had to describe yourself in three words, which ones would you choose?
  1. Do you hate any of your personality traits? Why?
  1. What are you truly obsessed about? Are you ashamed of it?

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  1. How often do you argue in the comments section with people on the internet?
  1. What is the funniest screw-up you have ever seen on Facebook or Instagram?
  1. Do you believe in soulmates? Explain.
  1. What is that one difference between the both of us that you absolutely adore?
  1. What is that one similarity between both of us that you absolutely love?
  1. Are you scared to love someone wholeheartedly? If yes, why?
  1. Where is your favorite place to hang out with me? Why?
  1. Is there any song that makes you think about me?
  1. Was it love at first sight for us? Can you describe the exact “a-ha!” moment you realized you have fallen for me?
  1. If you had to give me a new nickname/pet name, what would you like to call me?
  1. Which trait of my personality drew you towards me?
  1. Were you nervous when we had our first kiss? Were you expecting it to happen?
  1. If (God forbid) our relationship came to an end, what is the one thing you would miss about me the most?
  1. What is the one thing you would like to change about our relationship?
  1. Who do you think is the vulnerable one in our relationship?

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  1. Do you like watching romantic movies? What is the most romantic movie you have ever watched?
  1. What is your favorite way of receiving affection?
  1. Do you prefer big weddings or small ones?
  1. What is your favorite way of showing affection?
  1. What is the sexiest fantasy you have ever had about the both of us?
  1. Do you ever want to settle down and have children? If yes, how many?
  1. In what ways do you think we both have changed since we first got into this relationship?
  1. What about both of us is exactly the same since we first got into this relationship?
  1. What does love mean in your dictionary? Explain.
  1. What do you visualize when you are kissing me?
  1. Would you be embarrassed to hold my hand in public?
  1. Do you like romantic sh*t like kissing on the neck, cuddling, and PDA?
  1. Did you ever think about kissing me before we had our actual first kiss?
  1. Which part of my body do you like the most? Explain why.
  1. Guess which part of your body I like the most.

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  1. Do you ever want to go skinny dipping with me? Would you be scared of getting caught?
  1. Would you ever take a shower or bath with me? Would you be shy?
  1. Do you think I am too clingy?
  1. Do you ever just think about me when I am not with you?
  1. What are the little things that remind you of me?
  1. Do you think there is such a thing as being too much in love? Have you ever felt that about anyone?
  1. What was your first impression of me when you saw me for the first time? Were you attracted to me?
  1. If I was sad, how would you cheer me up?
  1. Do you want a future with me? Why?
  1. What is the one quirky thing about me that you adore?
  1. Did you ever think that I looked completely crazy in an outfit of mine? If yes, which one?

Infographic: 10 “Would You Rather” Questions To Ask Your Boyfriend

While you are on the quest to get answers from your boyfriend and make a fun time out of it, why don’t you make a game of it as well and play “Would You Rather” with him?

Check out this infographic for 10 cute and romantic “Would You Rather” questions to ask him.

10 would you rather questions to ask your boyfriend [infographic]

Illustration: StyleCraze Design Team

Communication is key to a long-lasting relationship. However, it is also only one area that most couples need to work on. People often find themselves stuck in awkward silence during their dates and struggle to continue conversations. In such cases, the above list of fun questions can help keep your talks exciting with your boyfriend and bring you two closer. The questions aim to reveal your partner’s quirky and intimate side and help you get to know their deepest selves.

That said, questions alone are not the solution to the communication issue. If your man is a bit closed off while communicating their feelings, you may have to push them a little to speak their mind. They may use one-word answers or even refuse to reply, making it troublesome to keep the dialogue going. Exercise patience in such situations and let them come out of their shell at their own pace.

Asking questions will also help you talk about otherwise difficult subjects to broach. Finally, be ready to ask lots of follow-up questions to gain further insight.

Each person is unique, so some of the questions may not work for your boyfriend. It is all about trial and error. So, sit together with some snacks and get ready for a session of discovery.

Frequently Asked Questions

What do guys like to talk about?

Most people like to talk about their interests and passions, be it music, sports, reading, documentaries, or even love interests. However, there could also be some deep and vulnerable conversations that can get you both closer in trust and companionship.

What are the 3 topics you should discuss in a relationship?

While that greatly depends on your life stage, your current circumstances, career, family, and finances are three essential things you must discuss openly with your partner to ensure you are on the same page.

Key Takeaways

  • The best way to build a deep and fulfilling relationship is by knowing each other well.
  • Asking fun questions to your boyfriend can help you figure out this personality and way of thinking.
  • You can ask him questions about his preferences, his day-to-day life, and life goals to understand him on a deeper level.

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As Head Of Content Operations, Harini sets the tone and editorial direction for StyleCraze to deliver engaging, interesting, and authentic... more

Dr Nancy B Irwin

(PsyD)
Originally from Atlanta, Dr. Nancy Irwin graduated from UWG in 1977 with a Bachelor of Music in Opera Performance. She... more

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