101 Fun Questions To Ask Your Boyfriend

Written by Harini Natarajan

The secret to a strong relationship is getting to truly know your partner. It doesn’t really matter whether your relationship is brand new or you have been together for a while. To build a deeper and more meaningful relationship with your love, ask him some fun questions to dig out the information buried deep within him. Confused about how to start off the whole thing?

First, light some candles and get some wine. As for the questions, you need not worry. We have done all the hard work for you, princess. Here is a list of 101 questions that cover almost all topics. Choose the ones that are applicable to your partner and get ready to get closer to him, both figuratively and physically! Don’t forget to have fun doing this!

101 Questions To Ask Your Boyfriend For Fun


  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?


  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?


  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?


  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?


  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?


  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.


  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?

Asking your boyfriend these questions will not only start a fun conversation but also help you get to know him better. For a relationship to stay passionate and last long, you need to know your partner inside out. There will be no bonding if you are not on the same wavelength.

But, men are known to be a bit aloof and closed off when it comes to communicating their feelings. Most of them use one-word answers, making it very difficult to keep the dialogue going. It can really feel like getting your teeth pulled! This method of asking questions will help you both talk about a particular subject in depth.

You need more than just small talk if you want your bae to come out of his shell, especially if he is the shy type. You also need to be ready to ask lots of follow-up questions as well. Every guy is unique, so some of the questions may not work for your guy. Find the ones that work for you both and get the conversation going! Have fun!

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As Chief Editor, Harini sets the tone and editorial direction for StyleCraze to deliver engaging, interesting, and authentic content revolving around women's health, wellness, and beauty. She has over 14 years of experience in content writing and editing for online media. She specializes in the areas of Beauty, Lifestyle, and Health & Wellness and is proficient in Medical Sciences (Biology, Human Anatomy and Physiology, and Biochemistry). Her background in Biomedical Engineering helps her decode and interpret the finer nuances of scientific research for her team. Harini is a certified bibliophile and a closet poet. She also loves dancing and traveling to offbeat destinations.