Best Questions to Ask Your Boyfriend

A lot of guys are not prone to opening up about themselves or their emotions. However, when one of them becomes your boyfriend, there is a certain level of opening up that must happen for the relationship to survive and feel healthy. 

That is the intent behind the following sets of questions. You may find that some questions get a one-word answer, and maybe you are okay with that, but I encourage you to have an open mind about asking follow-up questions to dig deeper.

As he answers, be aware of how he feels towards the question you are asking. Maybe he needs to be with you for longer to open up about some of the things these questions pry into. Gauge his mood and his answers to guide you with these questions. We have provided you with several categories to choose from, depending on what you really want to know about your man and what you feel he is willing to share.

Best Questions to Ask Your Boyfriend

Feel free to begin at the first question, or use his answers to guide you to different topics available here. You can click on the links below to jump to other topics if you feel the topic you are on is done or too sensitive for him. I hope you enjoy the experience of becoming closer to your boyfriend as you share the conversations this list will inevitably spark.

Best questions to start with | Fun questions | Entertainment questions | People in his life | Personal questions | His past | His worldview | His relationships

 

Best Questions to Start With

1. What’s your favorite waste of time?

If there’s one thing every person can relate to each other over, it’s procrastination.

2. What’s the best piece of advice you’ve ever received?

Everyone has gotten life tips from someone.

3. What’s your biggest pet peeve?

This is a quick and sure way to make sure you aren’t annoying them.

4. Hotdog or hamburger?

Food questions are always a yummy way to go.

5. Ice cream or milkshake?

Rapid-fire preference questions like this, and you’ll get your second and third date ideas before you know it.

6. If you could have one thing for breakfast every day, what would it be?

Breakfast is always a light conversation topic.

7. If someone had something in his/her teeth, would you feel comfortable telling them?

The way they answer this question will tell you a lot about them.

8. What’s something that you’d consider to be a waste of money?

We all have our ways of justifying purchases.

9. Would you consider yourself to be an introvert or an extrovert?

You’re going to want to know this about him before getting into a relationship.

10. What’s your favorite outdoor setting?

Beaches or backwoodsy? Forests or fields?

11. What do you think about when you’re alone?

This is a deep question, but it bears discussion.

12. How’s your life been lately?

Keep it sweet and simple.

13. If you could visit anywhere in the world right now, where would it be?

World travel is one of the most interesting conversation topics.

14. What’s something that no one else knows about you?

If you’re looking to relate to your partner on some deeper level, it’s important to share these kinds of personal things.

15. If you see a homeless person asking for money, do you give them any?

The way they answer this will reveal a lot about their character.

16. What would you NOT do for 5 million dollars?

There are some extreme lengths people will find themselves going to when it comes to money.

17. If you could fit your life into one picture, what would it look like?

This would definitely be an interesting work of art.

18. What’s your most prized possession?

Something you don’t think you could live without, couldn’t put a price on.

19. How do you like to relax?

Are you more of a “settle in for Netflix” type of person or a “kick back with a book at the beach” type?

20. What is your favorite color?

Definitely don’t make this the first question you ask, but always make sure to ask it.

21. What’s something that makes you feel crazy?

Whether it’s conspiracy theories or too much sweetener in your coffee, we all have that something.

22. What is a favorite dish you like to cook?

Is food a good way to bond?

23. Do you have things you do when you are having a bad day?

Does he realize when he is having a bad day, and does he take the initiative to make it a better day? 

24. How do you handle confrontations?

You are sure to have disagreements, so find out how he deals with them.

25. Do you have any debt you owe?

This is a good thing if you are considering furthering the relationship.

 

Fun Questions

1. Where is the craziest place you’ve danced?

2. What’s something stupid that you consider yourself to be really good at?

3. Do fish have necks?

4. What silly kinds of things do you do when your brain is on autopilot?

5. What’s the grossest food combo you can think of?

6. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?

7. What kind of vegetable would you be?

8. What’s the weirdest celebrity crush you’ve ever had?

9. What would your dream mansion look like?

10. What’s the worst date you’ve ever been on?

11. What ice cream flavor fits your personality best?

12. If you could have any superpower, what would it be?

13. What would you name a boat you owned?

14. If you could pick the most epic name to rename yourself, what would it be?

15. If you were to become rich suddenly, what would you do first?

16. What would your secret lair look like?

17. What inedible thing do you think would taste good if it were edible?

18. What would you do with your life if money and work weren’t factors?

19. What would you do if you were in zero gravity?

20. What’s the funniest screw up you’ve seen on social media?

21. Would you rather live in a cave or under the sea?

22. What was fun once, but you’ll never do it again?

23. Who’s your favorite YouTuber?

24. If you were a comedian, what act would you put on, or what funny stories would you tell?

25. Are you a roller coaster person?

 

Entertainment Questions

1. What’s the most binge-worthy show you watch?

2. In your opinion, what is the greatest film of all time?

3. If your life were a movie, what would it be called?

4. What’s a TV show you could watch over and over and never get tired of it?

5. What celebrity, past or present, would you want to have lunch with?

6. What’s the shortest amount of time you’ve binged an entire series?

7. Who is your favorite cartoon character?

8. With which MCU hero do you think you’re most similar?

9. When was the last time you had a movie marathon?

10. What kinds of situations make for the best podcasts?

11. What kinds of books do you read?

12. What have you spent quarantine doing?

13. What’s your favorite app?

14. Do you have a favorite podcast?

15. If your WiFi went out, what would you do to pass the time?

16. What’s something that calms you down?

17. What are some films that you’ve watched more than twice?

18. Do you watch soap operas?

19. Are you of the opinion that TV makes people stupid?

20. Are you someone who talks a lot during movies and TV shows?

21. How much does your love/hate relationship with reality TV shows fluctuate?

22. What is your favorite board game?

23. What sports can you not stand watching on live TV?

24. What’s your favorite album of all time?

25. What was the last concert you attended?

 

People in His Life

1. What qualities does your best friend have?

2. Which of your friends do you think you are most similar to?

3. How important is your family to you?

4. Do you think you would ever want to have kids?

5. What kinds of things make you relatable to other people?

6. What’s your favorite memory with your father/mother?

7. Are you the kind of person to prioritize other people above yourself?

8. What was your parents’ relationship like while you were growing up?

9. Who are you most afraid of losing?

10. Do you prefer to spend more time with your family or your friends?

11. Who is the most important person in your life?

12. Who’s one person you can talk to about anything and everything?

13. Who is someone in your life that consistently raises the bar for you and helps you do better?

14. What type of people annoy you the most?

15. Are you in touch with any of your old school friends?

16. Do you think men or women make for better friends?

17. Do you have any internet friends?

18. In your opinion, what’s the best way to meet new people?

19. Who is the first person you want to tell when something good happens? When something bad happens?

20. Do you think there is such a thing as too many friends?

21. What kinds of people do you think you surround yourself with most often?

22. How long do you have to know a person before you feel comfortable enough to touch them or try to hold their hand?

23. When you don’t feel like being around anyone, who will you most likely be okay with seeing?

24. Do you judge people by their words or by their actions?

25. Who in your life would you give both second and third chances to?

 

Personal Questions

1. What’s a life milestone that made you more mature as a person?

2. What’s your biggest regret?

3. What’s something you believe that most people don’t?

4. What’s your favorite childhood memory?

5. What’s something you’ve never told anyone?

6. What makes life worth living to you?

7. What’s something that makes you happy?

8. Do you think it’s possible to live up to your potential fully?

9. What are some of your quirks?

10. If your house were burning down, what would be three things that you’d want to grab first?

11. What’s something you’d consider yourself to be a snob about?

12. What’s your favorite type of music?

13. How curious are you?

14. What makes you feel alive?

15. What’s one thing you would never change about your life?

16. What are some of your favorite traits about yourself?

17. Would you say you might easily change your opinions?

18. Do you prefer to listen to your head or your heart when making important decisions?

19. What is something on your buckeye list?

20. In what situations do you act least like yourself?

21. What word describes you better than any other?

22. What do you hope to get out of life?

23. Would you consider yourself adventurous?

24. What do you consider to be a wasted life?

25. What’s one lesson in life that you had to learn the hard way?

 

His Past

1. What were you like as a kid?

2. Did your family ever go to family reunions?

3. Who did you look up to as a kid?

4. Have you ever held a grudge?

5. When you were younger, what’s one thing you looked forward to gaining in adulthood, but once you got it, it wasn’t all it was cracked up to be?

6. What was the weirdest part of your childhood?

7. What kinds of valuable lessons have you learned from past friendships and relationships?

8. In the past, have you been happier single or in a relationship?

9. Do you think the people that you have known in the past remember you or have forgotten you?

10. What used to cause you to get into the most trouble with your parents?

11. How did you use to spend summer breaks?

12. What was the best vacation your family took when you were younger?

13. Do you have any family holiday traditions?

14. What sort of rules did you have in your house growing up?

15. What was the best birthday you ever had?

16. What has been one of the biggest purchases you’ve ever made?

17. What’s a compliment that you received in the past that has stuck with you for a long time?

18. What has been your longest-lasting dream?

19. Where would you consider home?

20. What’s something that you were insulted about once that still makes you self-conscious now?

21. What has been the hardest period of your life?

22. What has been the greatest period of your life?

23. What was the first car you ever owned?

24. Have you ever received a speeding ticket? If so, what’s behind the story behind it?

25. What was the first job you ever had?

 

His Worldview

1. What are your thoughts on quitting your job to travel the world?

2. What are your political views?

3. What would you consider to be the nature of the world around us?

4. Do you believe in God or the Divine?

5. What do you think happens after we die?

6. Do you think it’s possible to know the absolute truth, or is truth always relative?

7. What is the line you draw between material reality and ultimate reality?

8. How do you measure right versus wrong?

9. Who in your life has had the most significant influence on your worldview?

10. What do you judge people for that you probably shouldn’t?

11. Do you think it’s important to face your fears or forget them?

12. What has had the most significant impact on your political beliefs?

13. What’s an issue that most people think is black and white, but you feel there is a large grey area on?

14. What’s a small thing people could do that would make the world a better place?

15. Would you rather be ignorant of some of the terrible things that go on in the world and stay happy, or be knowledgeable about some of the horrible things that go on in the world and never be entirely content?

16. What’s something you think is worth going to war over?

17. What are five subjects you think everyone should know a lot about?

18. How would you react if there was irrefutable proof that God doesn’t exist? What if there was irrefutable proof to the alternative?

19. What kind of event would you rather die than live through?

20. What kinds of experiences shape who you are?

21. What does the ‘American Dream’ mean to you?

22. What are some morals you live by?

23. What’s a global issue you’re tired of hearing about?

24. Do you believe everything happens for a reason?

25. What do you define as spirituality?

 

His Relationships

1. What’s an attribute you look for in a potential partner?

2. Do you believe everyone has a soulmate?

3. Does the word ‘love’ scare you?

4. What kinds of differences do you think are healthy to have between two people in a relationship?

5. Do you believe in love at first sight?

6. Do you think it’s important to be vulnerable in a relationship?

7. Do you think it’s okay to have certain secrets from each other while in a relationship?

8. What’s one quality you feel is important to look for in a partner?

9. Do you have any enemies?

10. What is an action someone can take to lose your trust completely?

11. Have you ever experienced heartbreak?

12. When you start a relationship with someone, what kinds of boundaries do you set for them and yourself?

13. Do you believe in second chances?

14. What do you think the people you love will say about you at your funeral?

15. How many serious relationships have you been in?

16. Is there anything you regret doing or not doing in a past relationship?

17. What’s the most valuable lesson you’ve learned from an ex?

18. What is the longest relationship you’ve had?

19. What are some qualities a man should have when he is in a relationship?

20. What are some qualities a woman should have when she is in a relationship?

21. Would you rather be perfectly happy but alone forever or remain unhappy with the love of your life?

22. Who’s someone that has had a massive impact on your political beliefs?

23. How big of a role do you think communication plays in a successful relationship?

24. What is the most serious relationship you’ve been in?

25. What do you think distinguishes relationship material from marriage material? What makes a relationship serious enough to put a ring on it?