Questions Game › To Ask Best Questions to Ask Your Boyfriend Questions GameWould You RatherTruth Or DareTo Ask by Lilyanne Rice Updated On Jan 07, 2020Regardless of how much you love your partner, you don’t know them completely. You might know most things about them, but there’s always something new to learn, don’t you think?It is no brainer that guys are the least expressive human beings; sometimes even less expressive than pets. Whilst this is the case, any good girlfriend should always strive to understand her boyfriend and make them feel wanted. And what better way to do this than asking questions?Read through our comprehensive list of deep, funny, sexy and dirty questions to tighten your relationship, develop that desired kinky aspect and generally activate some soul intelligence!Deep Questions to Ask Your Boyfriend1: Ever since you became an adult, what has been the most distinct blessing in disguise?Such a polite question to start any deep question game. Stay open-minded on this one, you just don’t know what to expect.2: What is one unique thing about this relationship that makes you overtly happy?You most probably know the answer to this, but a little pretense wouldn’t hurt.3: If you had no fear for a whole day, what would you try out first?Though it falls under the ‘deep’ category, this question could spark a funny or interesting conversation. Keep it light but learn something from it.4: What was your first honest impression when you laid your eyes on me?The worst you could do is get your hopes up with this one. Expect anything, especially because you were both strangers.5: What’s your greatest fear when it comes to us?You could use this as a cue to mention other things you fear happening to your relationship.6: What are some of the things you would never change about your life? Even if you were to change them for me?You’ve probably noted some of these things, but it’s time to discover more. A true test of principles and character.7: What do you think should be taught in institutions but isn’t it?Here’s a real foreshadow of what your kids will learn from their dad.8: How much do you think we have changed since our first date?There are numerous ways of evaluating growth. Leave it open-ended and test your partner’s creativity.9: What is one thing you are ashamed of about your past?This is by far, one of the deepest questions in this category. The answer partly depends on your tone, so make sure you know what you are doing.10: Without thinking too hard, what do you feel is the most affectionate thing in this relationship?If he loves and cares about you, you’ll have dozens of answers within no time.11: Tell me one thing I do that disgusts you and one that makes you feel good?Use this as an opportunity to table all your complaints, or else you might just have to forever hold your peace.12: As a couple, what do you think is our greatest weakness?Trust us, this might get him by surprise, so give him the time he needs. Rest assured, you will come up with more than one weakness. Such a nice way to grow!13: What is one underrated value you would teach a young professional?This is mostly applicable if your boyfriend is an experienced professional in a given area. If not, skip to the next one.14: How do you think we are special, compared to other couples?Depending on how well you know other couples and their mannerisms, you can come up with several answers.15: If you could get two roundtrip tickets with me, where would you want to go?This is deep in the sense that you are testing whether your boyfriend knows some of your dream destinations.16: What is the one memory that brings a smile on your face regardless of the situation you are in?Time to relive all those happy moments and rank them to their order of greatness.17: Given a chance, would you have an open relationship with me?If your boyfriend is the serious, committed type, then they may read this the wrong way. Be careful!18: Would you rather be the wisest or richest person alive?Don’t stop at either choice. Learn why he chose his answer and try to understand his thinking.19: Do you believe in fate and that everything happens for a reason? Especially when it comes to affairs of the heart?It’s a matter of having a rich mindset and seeing things objectively. Does your boyfriend see things logically or is he engrossed in fairytales?20: Which is the one dream you can’t seem to get over?Dreams are the easiest things to forget. If there’s one he remembers clearly, then you should take note of it.Fun Questions to Ask Your Boyfriend21: If you had an option to have dinner with anyone in the world, who would it be?Use this to tease around with his favorite celebrities and learn how he ranks them.22: What would you change about your lifestyle if you knew you were going to die in one year?This could escalate quick. Maybe leaving you could be one of his resolutions. Keep it fun and light though.23: After saving your loved ones and pets in a house on fire, you have an opportunity to save one more item. What would it be?Could it be his video games? Your favorite souvenir? You’ll never know if you don’t ask.24: If you were to be the most famous person since the existence of mankind, in what way would you want to be known?If he is sporty, you might have a hunch of what he would say. But you never know: People’s perception of fame is different.25: For the last 60 years of your life, would you rather retain the mind of a 20-year-old or the body of a 30-year-old? And why?This easily qualifies as one of the most hilarious questions on our list. The ‘why’ is what matters.26: What is one crazy thing you have always dreamt of doing but have never had the chance to? When do you think you’ll do it?Don’t settle for one. Laugh over the absurd ones and note down the doable ones, then help him achieve them.27: What is one embarrassing moment about your life that I am not aware of?Depending on your boyfriend’s personality, you might get a good hard laugh, or end up sad about the embarrassing moment.28: If you had a mirror that showed you what happened in the past or what will happen in the future, what would you opt to find out?Again, this entirely depends on his traits. Would he rather live in the past or speculate on the future?29: Assuming you can only eat one type of meal for the rest of your life, what would it be and why?This is the best opportunity for you to learn conclusively, what his best meal is.30: If you were to wear a dress or put on makeup for the rest of your life, which one would you choose?Both can portray one as gay. Which one is less shameful?31: What kind of weird superpower would you like to have if you were given a chance?Make sure to give ample time for this one. Especially if your boyfriend is a geek.32: Growing up as a teen, who was your celebrity crush? If you were to marry them right now, would you?There’s no room for jealousy on this one. Though anything is possible, including marrying a celebrity crush.33: If you had the chance to invent something that would sell worldwide? What thing would it be? Food or technology?Expect some crazy answers here. Most people would rather be known for weird items rather than the normal ones.34: Let’s say you were invisible for 24 hours. What is the first thing you would do?Help him speculate and weigh his options. Especially when it comes to stalking people.35: Given the chance to rename and re-design all your favorite animals, how would you do it? And what would you name them?Notably, this is the one fun question that will trigger his creativity. Laugh at the endless possibilities of this.36: You are supposed to make a public romantic dance in front of all the closest people in your life. But you are supposed to either do it with my dad or your dad. Who would it be?The real question should be, who would he rather embarrass? His dad or your dad? We both know the answer to this.37: Between pretending to be an animal and pretending to be a woman, which one would you pull off comfortably?Almost puts him between a rock and a hard place. Either way, people will still think of him as a madman.38: Would you opt to be a movie star or the most talented singer?Glamour, glory, and fame, but in different forms. You should even form stage names after this.39: What did you want to be growing up? How different is it from what you are right now?The best thing about this is that you can help him speculate how life would have been and if you would have met?40: If you were to choose between joining the armed forces or being an astronaut, what would you choose?Both options pose great risks, in a fun way, but are not equal.Sexy Questions to Ask Your Boyfriend41: If you were to dress me, what outfit would look best on me?This is such a moderate question to kickstart a sexy conversation.42: Do you think of yourself as a decent kisser?You both know the answer to this but what matters is understanding his point of view. Tell him if you like it or not.43: Where and how do you like being touched the most?Make it even more fun and offer to do it right there and then.44: What is the one way you like being teased but haven’t gotten from me?Learning new things about your partner could help you exploit each other’s full potential.45: What is the ideal role play for you? And for how long?If he has been watching naughty things, expect a wide array of answers.46: Tell me one thing that turns you on almost instantly?This should be easy. Considering guys get turned on much faster.47: If you were to choose what age to lose your virginity, what would it be?If it’s too young, you should be quick to tease how perverted he is.48: What usually runs on your mind during your solo time?There are high chances you are not the one who runs on his mind.49: If you could be with one celebrity for the rest of your life, who would it be?Interesting but hard; especially with the numerous beautiful celebrities of today.50: Have you ever thought of going skinny dipping with a group of friends? Or have you ever done it?This is one of the most embarrassing in the bunch. If he has done it, then he has the greatest guts.51: On a scale of 1-10, how much would you rate the effect of hickies in the whole process of lovemaking?Maybe your boyfriend doesn’t like the norm? There is only one way to know.52: Ever since we started dating, have you ever made out with me in public to make someone else jealous?People do all sorts of things to make others jealous. It would be so satisfying if he has done it.53: Have you ever gone to a strip club? And why?Just make sure it’s all part of his past. Otherwise, you would have a hard time keeping him from straying.54: When was the first and last time you had a dream about me? What was it about?This could be hard to remember especially if you have been together for long. If you haven’t dated for long, don’t be surprised to get zero occurrences.55: What is the most daring thing you’ve done on a first date? Did it bring the results you expected?Maybe you never knew your boyfriend as much as you thought. This should be an eye-opener.56: Assuming you had the most accurate x-ray glasses, which part of me would you look at first?This sets the mood on a whole different level. Don’t be surprised if things got heated up after this.57: What is the one thing you have always wanted me to do but I have never done?If it’s something you can help him achieve, then, by all means, make his dreams come true.58: If you could use one word to describe the taste of my lips, what would it be?Fruits? Meat? Perfumes? The options are endless. This could help in boosting fantasy between the two of you.59: In the real world, which movie scene would you like to recreate with me?If possible, do it there and then, and continue with the game.60: As strangers, what would be your first reaction if I showed up at your doorstep in bikinis?To get things into context, make him jump into action and illustrate.Dirty Questions to Ask Your Boyfriend61: In your many years of experience, have you ever used a lubricant? Would you use it with me?Easily one of the trickiest questions. Pray your boyfriend is into kinky stuff.62: What is the one outfit you have been dying to see me in?Keep your mind open to this one. You might just get something new.63: Tell me exactly what is running through your mind?He might as well make up something to match the mood, or he might tell the truth. Who knows?64: Which one would you choose between a deep sensual massage and a strip teasing session?If you feel like taking things up a notch, this is the ideal question.65: What are some of the craziest fantasies you’ve had with me?Only one piece of advice for this question: Be prepared for anything!66: Do you like getting kinky with bright lights, dim lights or complete darkness?Compare notes on the advantages of each and settle down on what to use in the future67: If I was to do anything you ask, what would you want me to do for you?His wish is your command.68: Describe in detail, exactly what you are wearing.When it comes to texting, this sets the pace for some lengthy naughty conversation.69: What was the last crazy or wild dream you had?If you are hot-tempered, don’t ask who the dream was about.70: Do you like it when I get extremely naughty or extremely submissive?It would be much better if he liked both.71: What is your preferred type of lingerie?Don’t expect him to know the lingerie by name. I’m sure he can describe it though.72: Where have you always wanted to kiss me?Make sure to ask this question if you haven’t been together for long.73: Do you think you can unhook a bra with using your mouth and with your eyes closed?There is only one way to find out. Ask him to do it practically and evaluate the results together.74: If you were to make a wild guess, what kind of panties am I wearing and what color are they?He could easily score this because he knows you well. Or does he?75: What is one risky fantasy you would like to try with me?It’s time to explore the wild fantasies in your boyfriend’s head.76: When was the last time you had a quickie?There is nothing to be ashamed of. Hopefully, the quickie didn’t happen with someone else.77: Have you ever sent nudes to anyone? How did it feel?If the answer is no, then you are one lucky woman.78: As far as the environment is concerned, what is your preference in lovemaking?There are endless possibilities here. Try them out after this.79: Have you ever wanted to kick something off with someone older than you?This is pretty weird, but it makes the conversation quite interesting.80: What do you want me to wear to bed tonight?Quick and straight to the point. If he doesn’t catch the bait, then nothing will.