302 Questions To Ask Your Boyfriend (Need To Know Answers)

When you are first starting out seeing a person, it can be so tempting to do one of two things. Firstly, you can get totally caught up in the fun and first rush of love so that you don’t see any of a person’s true colors. You tend to just get swept up at the moment – perhaps by his romantic gestures or other things that make you feel the first shoots of love which can be a very addictive feeling. 

The second thing that we can do is to want to get to know a person inside out before we embark on a fully-fledged relationship with them. The problem with this approach is that it can be incredibly intimidating to someone you are seeing. Regardless of whether you want him in your life for a long time as you think that you may like him enough that they will be the one for you, they may not necessarily realize how you are thinking. The result is that they may be put off the relationship due to the intensity that it begins stemming from your want to familiarize yourself with him so well.

Bearing this in mind, there are a number of questions to ask your boyfriend that are fine to ask, but sometimes it may be worthwhile doing so with some restraint. Good-humored inquisitions can be a great and direct way of getting answers from someone you think you could love in the future, but being asked them without those queries being framed in the guise of a game can be incredibly overwhelming and off-putting to a person. You may make the person you like think that you are a far more serious and intense person than you are. 

That being said, sometimes it does pay to get to the nitty-gritty of a person’s character at the beginning of a relationship so that you do not waste your time on someone that in reality, you do not want in your life.

Remember therefore that there is a balance to be had when looking at questions to ask your boyfriend. You’ll realize best what that balance is as you will have the best stance on what your guy would like and what he would not enjoy. 

What Questions Should I Ask My Boyfriend?

Below, we have listed 302 questions to ask your boyfriend that can be a great way to get to know them. We’ve separated them into sections so that you can pick and choose questions from each. Or you can just choose to ask all the questions from one section if there is one element of your guy’s character that you want to familiarize yourself with more. 

For example, we have a whole section dedicated to relationship must-knows where you can find out the innermost thoughts that your guy has when it comes to his approach to relationships and girlfriends. There are also questions there that can help you understand why he acts in certain ways now due to things that have happened to him any one of his relationships in the past. 

We also have a whole section dedicated to questions to ask about a person’s sex life and sexual past. This may or may not be important to some people, whereas to others it can be helpful knowing what makes a person tick in the bedroom at the start of a relationship. Additionally, it may help you realize whether you are sexually compatible with the guy you are trying to start up with. 

Our other sections include queries to ask about his friendships, his mates, as well as a section regarding his family and family members. It is in this section that you will find queries regarding his childhood which can be very enlightening as to a person’s character and why they may react to things as they do now in the present. 

Cute Questions

In this section, we list some cute questions to ask your boyfriend that can be good and fun to ask and also help you know the little things about him that may otherwise take you a lot of time to realize. 

Cute questions to ask your boyfriend are the perfect things to ask them at the beginning of a relationship as they can be quite fun in character and will often spark conversation. In doing so, you will see whether you are compatible with each other even more quickly and whether he is really someone that you can envisage spending your life with. There will always be something that you find out about someone when you ask the following, even if it is knowing what their favorite thing is when it comes to any number of areas of his life. 

As ever, when it comes to asking these, be sensitive to how well your other half is taking the line of questionings. While they are all said in jest and good humor, it could be that someone you are seeing would like a break at times in how long their questioning goes on for! Bearing this in mind, cute questions to ask your boyfriend are usually always fine to ask – but sometimes remember that you may want to ask them in small doses, depending on how you think your other half feels. 

1. Where did you have your first kiss?
2. Who was your first crush?
3. What has been your favorite kiss of all time?
4. What are your signature first date moves?
5. Have you ever dated a famous person? 
6. What’s your favorite alcoholic beverage?
7. What is your favorite Beatles song?
8. What was your favorite thing to play as a child? 
9. What would your last meal on death row be? 
10. What is your dream job? 
11. If you could own any car in the world, what would it be? 
12. If you could have invented anything in the world, what would it be? 
13. If you had to get takeout from one restaurant for the rest of your life, what restaurant would it be?
14. What do you find most attractive and appealing in a woman? 
15. What is your favorite TV show? 
16. How do you take your coffee?
17. What is your hangover cure?
18. What drink can you no longer stand the thought of after getting too drunk on it once?
19. What is the one thing that you feel you should have done differently in the past? 
20. What is your all-time favorite film to watch over and over again? 
21. What did you want to be when you were younger?
22. What’s the silliest thing that you can do? 
23. If you could meet one deceased famous person, who would that person be? 
24. Would you choose to learn about your future if you could be told it? 
25. What is the most ridiculous thing you’ve ever done? 

Personal Questions

Without a doubt, personal questions to your boyfriend can sometimes be difficult to say out loud and also difficult to ask. And while some of the questions to ask your boyfriend that we have listed below are not essential to know for a relationship to be successful, they may actually get you into thinking about your boyfriend in a different light. 

When it comes to personal questions to ask your boyfriend, like the ones we have listed below, some of the questions will be easier to ask than others. Also, remember that some people will be more sensitive to some questions than you realize so asking them may require more tact than you may realize. This is particularly the case if you are at the beginning of your relationship with a guy and you are still figuring each other out a little. 

Bearing that in mind, try to take a relaxed approach with these personal questions to ask your boyfriend – especially if you don’t really mind exactly what his answer is, and that you are just asking for some light entertainment. The reason being is that you may stumble upon a question that does bring up some deeper-seated issues in him than you would have never expected. 

As ever, be sensitive and respectful of a person’s thoughts and wants and you should find that you get to know what you want, without hurting the person or people you love most. 

1. Do you always leave things to the last minute or do you plan way in advance? 
2. Have you ever dyed your hair? 
3. Have you ever had a piercing?
4. Would you ever get a tattoo? If so, what would it be? 
5. What’s your biggest celebrity crush?
6. Who would you want to play you in a film?
7. What is your signature dish?
8. When you were in school what was your best subject?
9. Do you think there is equality of the sexes?
10. What’s the one and only book you could read for the rest of your life? 
11. What is the one thing that always makes you smile, every time you see or hear about it? 
12. Who is your favorite person to follow on social media? 
13. What is your most hilarious guilty pleasure or habit that you just can’t stop, no matter how many times you try? 
14. What has been the most embarrassing thing to happen to you? 
15. What is the kindest thing that anyone has said to you in your life? 
16. Have you ever lied on your CV or resume? 
17. Tell me something that you have never admitted to anyone. 
18. Would you prefer to watch Netflix or go out on a Friday night? 
19. What is your weirdest habit that you do all the time? 
20. If you could, would you change your weirdest habit? 
21. What are you most excited about doing when Saturday morning rolls around?
22. Do you have any scars that no one else knows about? 
23. Would you change your hair color forever if you could? 
24. What is the most disgusting thing that you have ever eaten? 
25. If you could go back in time tomorrow, what would you tell the 12-year-old you? 

Would You Rather Questions

These types of questions are meant to be a bit of fun and questions to ask your partner when you are perhaps a little bit bored and looking for a bit of amusement. They won’t ever go more than skin deep but you may learn a couple of things about your other half that you wouldn’t have otherwise known. 

This isn’t an exhaustive list either – some people love to play would you rather make car journeys go even more quickly. If you are ever stuck for questions to ask your boyfriend in a game, a good way to come up with questions to ask is to think about his favorite TV show and go through the characters. Ask him who he would rather be, or who he would rather sleep with or anything else you can think of. The list is endless and only ever limited by your imagination. 

You may want to get comfortable too – once you get on a roll with this game, it can be hard to stop! It can be a lot of fun and can pass the time very easily when you are bored or in the mood for some light entertainment with the guy that you love. 

1. Would you rather be hot or cold?
2. Would you rather date a blonde or a brunette?
3. Would you rather have a cat or a dog?
4. Would you rather marry Rachel or Monica from Friends, the TV show?
5. Would you rather be beautiful or clever?
6. Would you rather look younger from the neck up or from the neck down?
7. Would you rather be the funniest person or the cleverest person? 
8. Would you rather fly or be invisible?
9. Would you rather be in love or be rich?
10. Would you rather be hungry or thirsty?

Questions To Get To Know Him Better

We all want to get to know a person we are in a relationship with as well as possible. Questions below will help your relationship by asking some superficial things but also much deeper things so you get to know a person inside out. As ever, remember to be tactful and sensitive to a person’s mood when trying to ask them. 

1. Would you ever choose a promotion over a relationship? 
2. How old were you when you lost your virginity?
3. Where were you when you lost your virginity? 
4. Have you ever stolen anything?
5. Have you ever broken the law?
6. Have you ever taken any drugs?
7. What shoe size are you?
8. What is your signature dish when it’s your turn in the kitchen?
9. If you had to choose a cuisine to eat for the rest of your life what would it be?
10. What is your favorite sport to play for a hobby?
11. What do you spend the most money on each month (not including rent)?
12. Where was the first place you lived when you left home?
13. How would you describe yourself in three words?
14. How many times did you have to take your driving test?
15. Have you ever hitchhiked?
16. What is the one thing you admire most about yourself?
17. What is the one thing you admire most about me? 
18. If you had to choose one person as your role model, who would it be? 
19. What is something you’ve never been able to do well? 
20. When you have had a very stressful day at work, how do you relax? 
21. What is the one thing you always notice first in a woman? 
22. What is the one thing you are least proud of doing in your life? 
23. If you could be a professional sports player, what sport would you choose? 
24. Would you prefer to have a sunny beach holiday or to have a vacation spent on the slopes? 
25. How would you choose to spend a day off, if you were given the day off tomorrow? 

Deep Questions To Ask Your Boyfriend

While thinking about questions to ask your boyfriend, it can be tempting sometimes too to shy away from deep questions, even though you may want to know some of the answers. You should definitely think about trying deep questions to ask your boyfriend as it can help you get to know them even better than you did before. 

Plus, you may find that you realize some incredibly important things that can materially impact how you feel about one another. For example, there may be an issue that arises due to his work and career, or something may come out of your deep questions that shed light on how he feels about your future together. 

Bearing that in mind, tread carefully when you come to ask your boyfriend questions that you may be afraid of knowing the answer. While it is always good to know all the facts about a person that can affect your future, you also need to ensure that your questions get you the answers you are prepared to hear. The deep questions to ask that we think provide answers that everyone in a couple should know are:

1. If you could change anything that happened in your life what would it be?
2. How important do you think sex is to a relationship?
3. Do you want children? If you have children, do you want any more? 
4. Do you ever think it is ok to lie to a person you are in a relationship with? 
5. If someone cheats on you, could you ever forgive them? 
6. What are the three essential characteristics you always need to see in people you are in a relationship with?
7. Do you believe in second chances? 
8. What is your biggest regret? 
9. What are your personal goals in life? When do you want to achieve them? 
10. Where do you see yourself in five years? 10 years? And 20 years? 
11. What are your insecurities and what makes you feel insecure? 
12. What are your goals professionally and with respect to your career? 
13. What’s on your bucket list? 
14. Do you believe in God? If yes, are you religious? If so, which one?
15. What is the happiest moment of your life?
16. What do you see as the bravest thing you have ever done? 
17. What is your idea of the perfect day? 
18. What is the kindest thing someone has ever done for you? 
19. What is something that you think we could all do to help stop climate change?
20. What is the one thing that you are most afraid of? 
21. What is the one thing that makes you most angry, every time it happens? 
22. What has been your greatest achievement in your life? 
23. If you could go to any politician’s house tomorrow to talk about an issue close to your heart, what would that issue be and who would be the politician? 
24. Would you want to know how you are going to die in the future? 
25. Would you want to get reacquainted with anyone that you have lost contact with? 

Fun Questions To Ask Your Boyfriend

While asking your boyfriend questions to get to know him better is a great way to strengthen the bond between you and him and can help you in figuring out whether you have a chance in the long term, it can also be a really good idea to ask him some fun questions too. If you only ask your boyfriend serious questions, he may find you quite intense and it may have the adverse effect of pushing a wedge between the two of you as opposed to bringing you closer. 

Remember to keep things light from time to time with the following questions to ask your boyfriend that will make you both smile and laugh, while all the time having fun. That fun should have the positive repercussion of bringing you closer and closer together as you will want to spend more time in each other’s company as the time you spend together is so enjoyable. 

Additionally, fun questions can also highlight parts of your love interest’s character that you may not have otherwise known. As you will see from the questions to ask your boyfriend that we have listed below, a lot of the answers are not answers that would have otherwise come up in the normal day to day conversation. In doing so, you again strengthen your bond as you get to know each other’s personalities and how each of you thinks.

1. Would you prefer to eat pizzas or hamburgers for the rest of your life? 
2. If you could change anything about your appearance what would it be?
3. How many times have you broken or lost phone? 
4. What is your biggest pet peeve? 
5. If you could go anywhere tomorrow where would it be? 
6. If you could go anywhere to live for the rest of your life where would it be? 
7. What’s the one thing you would exchange a winning lottery ticket for? 
8. What was your first car? 
9. What was your first job?
10. Would you want to be famous?
11. What’s your favorite song of all time? 
12. What is your favorite food? 
13. What do you think is the biggest way to waste money? 
14. What was your favorite character as a child? 
15. What is your favorite type of animal?
16. What was the name of your favorite pet? 
17. What’s your preferred form of social media?
18. What is your all-time dream job? 
19. Who do you think played the best James Bond?
20. What is the strangest thing that has happened to you on a date? 
21. What would be the worst thing a person could do on a date to turn you off completely? 
22. What is the one thing that you love best about the place you currently live in?
23. What is the one thing that you wish you could change about the place you currently live in?
24. What is your zodiac sign?
25. If you had three wishes from the genie in the lamp, what would you choose them to be?  

Random Queries To Keep Your Boyfriend On His Toes

In any relationship you have with a person, you will find out the small and trivial things in a number of ways. Asking the below, you will find out quickly some really random things about the guy you are in a relationship within the most direct way possible. 

1. What is your preferred high street shop to buy clothes in?
2. If you inherited a billion dollars tomorrow, what do you think you would do with it? 
3. What is your favorite quote? 
4. Do you like to think that everything happens in life for a reason? 
5. If you woke up one day and no longer suffered from fear or anxiety, what would you like to do first? 
6. Do you think you’d prefer to be blind or deaf? 
7. Finish this sentence: My relationship with my partner is something that could be improved by __________
8. What is the one thing that when you think of it, always makes you smile? 
9. What is the one thing that will never fail to make you angry when you think of it? 
10. What do you think of as your biggest relationship mistake? 
11. Do you think it is possible to be in love with two people at the same time? 
12. How do you think I like to take my coffee? 
13. How do you think you make decisions in your life? Do you go with your gut or do you think things through? 
14. Do you have any relationships in your life that sap you of all energy? 
15. What would you do for your most perfect day? 
16. If you could eat something that is really bad for you without worrying about your health, what would it be? 
17. What are you most grateful for? 
18. What’s the biggest lie you have ever told? 
19. What do you love to do on your own with no one else watching? 
20. If you could speak another language, what would you love that language to be? 
21. What is your favorite book?
22. What is the favorite part of your day?
23. What do you love to do just before bed? 
24. Have you ever been in a relationship where you were in love, but the other person wasn’t? 
25. What was the last thing that made you laugh out loud until your sides hurt? 

Relationship Questions To Ask Your Boyfriend

By asking the below you will get to the bottom of how your boyfriend acts in a relationship very quickly. His answers to the following will help you explore how he has acted on his past relationship that was important to him and how he has dealt with previous relationship disappointments. 

1. Have you ever cheated on someone? 
2. Have you ever been cheated on during a relationship? 
3. Have you ever been in love with someone? 
4. Have you ever had your heart broken by someone before? 
5. What is the most romantic thing you have done for someone? 
6. Have you ever been married? 
7. Do you believe in marriage? 
8. What is the most important thing you think is necessary to have in a happy and healthy relationship?
9. Do you value intelligence or looks more in a relationship?
10. How long do you wait to have sex with someone you are dating? 
11. Do you believe in love at first sight?
12. Do you believe in soulmates? 
13. What do you want from a romantic relationship?
14. What do you expect as a standard in the behavior of your partner? 
15. How many sexual partners have you had?
16. Have you ever slept with a person of the same sex? 
17. What do you tell women you are dating as a way to impress them? 
18. What would you want to know about your partner from the beginning of your relationship? 
19. Have you ever quoted a line from a film to impress a girl? 
20. What would you say were your good points as a boyfriend? 
21. What would you say were your bad points as a boyfriend? 
22. What has been your biggest regret about your past relationships? Would you change it if you could change the past? 
23. If you could change anything about how you behave in a relationship with someone that you love, what would that thing be? 
24. If you always had to pick, would you choose to go on a romantic holiday or a mates’ holiday?
25. Would you tell me your biggest secret? If not, why? 

Questions About His Family Life

A person’s relationship with their family is crucial as it forms the basis of how they approach all other relationships in their life. Asking the below may shed light on how your boyfriend will react to things between the two of you in the future, or you may learn why they act in certain ways. 

1. How would you describe your childhood in five words? 
2. Would you change anything about your childhood? 
3. Are you closer to your mom or your dad?
4. Who is your favorite sibling? (if he has one)
5. Would you describe your relationship with your family as a good one?
6. What has been the most upsetting thing to happen to your family? 
7. Did you admire your parents’ relationship growing up? 
8. Would you ever break up with a person and end a relationship, if your family didn’t like your partner? 
9. What is the meanest thing you’ve ever done to a sibling?
10. What’s your earliest childhood memory? 
11. Are your grandparents still alive? If yes, how old are they? 
12. Have you ever lost a family member? 
13. Did you have pets as a child? 
14. How often do you see your family members?
15. Where do your family members live now? 
16. Do you get along with your parents? 
17. What was the last thing you said to your parents the last time you spoke to them? 
18. Would you like your family if you weren’t related to them? 
19. Did you and your family have a favorite place that you used to go to all the time? 
20. Who do you look like most – your mom or dad? 
21. What was your favorite thing to do with your family when you were growing up? 
22. What was your relationship like with your grandparents when you were growing up? 
23. What was the one thing that you remember most about your childhood? 
24. What is the biggest secret that you have kept from your parents? 
25. Would your parents describe you as a good child or a naughty one? 

Questions To Ask About His Friends

Knowing how a guy feels about his friends is actually a great way to get to know them so much better. How people act around their nearest and dearest as well as what they do for those very people, is a good indicator of what a guy is truly like. It can give you a great idea about what he will be like if your relationship is for the long term and you can make a decision on whether you think you will work as a couple or not, often by simply knowing how he behaves towards his friends and how he deals with friendships. 

Here, we look at questions to ask your boyfriend that will get to the bottom of what he is like around his best mates and how he has behaved towards them in the past. Some of the answers will be really enlightening as great questions can really make you think differently about a person if their answers surprise you. 

While some of our questions to ask your boyfriend that we have listed below are a little tongue in cheek, some will get to the very bottom of how he treats friends and whether he is sorry for any mishaps with friends in the past. For, while everyone makes mistakes, it is good to know that if your guy has done something wrong with a friend in the past, he at least shows some remorse for it.  

1. Who is your best friend? 
2. Why is your best friend, your best friend? 
3. How did you meet your best friend? 
4. Have you ever lied to a friend?
5. Would you choose a friend over a crush?
6. Have you ever been jealous of one of your friends? 
7. Have you ever bailed on plans with your friends to go out on a date? 
8. Would you ever bail on plans with a date to go out with your friends? 
9. Do you need your friends to approve of the person you are dating? 
10. Do you still keep in contact with anyone from school? 
11. Do you think it is possible to be very good friends with people you work with? 
12. Have you ever crushed on a friend’s significant someone? 
13. How do you think your best friend would describe you? 
14. What is your favorite thing to do with your friends? 
15. What one thing do you wish you and your best friend did more together? 
16. What is your favorite bar to go to with your friends? 
17. If you have children, do you have any mates that you would not like to babysit? 
18. Do you think you have a good relationship with your best mates?
19. Do you feel you have to work at your relationship with your mates or do they just take care of themselves?
20. If you feel you are in a bad place, relationship-wise with a friend, how do you go about resolving the situation to make you both feel better? 
21. What is your mates’ favorite or the best way to pass the time? 
22. Have you and your best mates ever tried to sleep with the same person? 
23. Is there one person in your friendship group that you don’t like? 
24. Do you feel it is possible to change a friend’s mind when he or she is in love? 
25. Do you ever feel taken for granted by your mates?  

Questions About His Sex Life

When you are in a relationship with a person, it’s important to know what you can about their sex life and their approach to it. It can really shed light on what they like and what you can expect in the future if your relationship turns into a sexual one. 

1. What’s your favorite sexual position? 
2. What is your favorite place you have ever had sex? 
3. What’s the most outrageous thing you’ve ever done in bed? 
4. What’s the most outrageous thing you’ve been asked to do it in bed? 
5. What’s the one thing that is your biggest turn-off?
6. What’s your favorite thing or turn on in bed? 
7. Would you give celibacy a chance if your partner asked you to? 
8. Do you have any sexual regrets? If so, what are they? 
9. Have you ever had a one night stand?
10. Have you ever slept with someone on the first date? 
11. Have you ever forgotten someone’s name while having sex with them?
12. Have you ever had a threesome? 
13. What’s the sexiest dream that you have ever had? 
14. Do you think sex or communication is more important in a relationship? 
15. Do you think that a relationship is possible to sustain without sex? 
16. If you found out that your other half had slept with a lot of people would you think differently of them? 
17. If you found out that your other half was a virgin, would you think differently of them? 
18. What is the one fantasy that you have not managed to do yet? 
19. Would you ever go without sex in a relationship if she or he didn’t believe in sex before marriage? 
20. What is your favorite type of foreplay? 
21. Would you ever go down on someone if you knew they would never return the favor? 
22. What was the biggest age gap you have had with a person you have had sex with? 
23. Is there something you would like us to try that you haven’t done with anyone else before? 
24. Do you think it is possible to have good sex if you are not in a loving relationship? 
25. Do you think that having sex is the same as making love? 

Questions For A Game Of 21 Questions

21 questions are meant to be a quickfire round of questions that are both deep and lighthearted. They can be about relationships or about something very superficial, but the general idea is that it is meant to be fun for you both. 

1. Would you rather be rich or famous? 
2. If you could be any superhero, what superhero would you want to be? 
3. What would you do if you won the lottery tomorrow? 
4. When you wake up in the morning, what is the one thing that you are excited about first? 
5. How do you spend your usual Saturday night? 
6. Do you have any hidden talents in your life that you never get asked about? 
7. What’s the one accomplishment in your life that you are most proud of? 
8. What animal would you be? 
9. What are you afraid of most in life? 
10. If your house was burning down, and all the people in it were safe, what three objects or things would you save? 
11. What’s your favorite joke you have ever heard? 
12. Would you ever want to climb Mount Everest? 
13. What is the one thing you regret most about not doing in your life? 
14. What is the funniest thing that has ever happened to you in the past? 
15. If you were ice cream, what ice cream would you be? 
16. What has been your favorite ever single purchase? 
17. What day of the week is your favorite and why? 
18. Would you like to change something about your life? 
19. Do you think you have ever experienced deja vu or the feeling that a day is repeating itself? 
20. How do you like to wake up in the morning? Talk me through your best morning routine.
21. What’s the one place you would like to go to in your life but think you will never get the chance? 

Here are some questions to change up and swap in if there are somethings that you don’t love about the ones above:

22. Do you feel it is possible to change a person?

23. If you could change your best trait to win $5million dollars, would you?

24. Do you like to plan in advance or do you like to leave things until the last minute?

25. If you were a member of the opposite sex for a day, what could you like to do? 

Bonus Questions To Ask 

1. Have you ever been in a co-dependent relationship? 
2. Do you think you have a healthy relationship with food? 
3. Do you think you have a healthy relationship with money? 
4. Who do you think has been your favorite president? 
5. What relationship are you most proud of? 
6. How old were you when you first fell in love? 
7. Do you love to dance when out clubbing or do you prefer to wait at the bar? 
8. What do you think is your biggest temptation? 
9. What song do you love to listen to? 
10. Is there a song that makes you cry?
11. What would you do differently from the last year? 
12. What conspiracy theory do you think is true? 
13. What is the one thing you don’t think you could live without? 
14. What do you love to eat for breakfast?
15. Do you believe in ghosts? 
16. How do you react to racism?
17. Have you ever been put in handcuffs? 

FAQs

Questions to Ask Boyfriend – The Bottom Line

Hopefully, you have found all of these questions really helpful for your purposes, whether you wanted to get to know your other half in a more profound and meaningful way, or if you simply want to get to know their little nuances and funny habits. Directly asking someone about his life is the easiest and quickest way to find out something about that person. Do remember that sometimes tact is needed. A blunt approach can sometimes be quite overwhelming.