175 Fun Questions to Ask Your Boyfriend to Know Him Better

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I think we can all agree that it is of the utmost importance to know all we can about our partner.  When in a dating relationship, the hope is that it could potentially turn into something more serious and permanent.

No one wants to become wholly committed to a person and later find out that you had different views on matters you consider to be “deal breakers.” If we are honest, we may find that we stood in a relationship with a person for a long time based on superficial reasons. That is no way to lay a solid foundation.

Gaining insight into your boyfriend's personality can reveal his true values and priorities in life.  It doesn’t have to be a tedious thing to ask these questions.  On the contrary, you’ll find after reading this article that it can be a fun and amusing way to learn about your partner on a deeper level.

Why Is It Important to Ask Your Partner Questions When Dating?

In any relationship, the goal is to make sure both parties involved are on the “same page” and grow together. Being on the same page ensures that you and your boyfriend have the same goals for the relationship.  Furthermore, it helps you avoid unpleasant surprises or potentially relationship-ending issues when your heart is fully invested in him.

You wouldn't want to seriously think about marrying a person who has no desire to be married at all.  Or you may not want to have children, but he may desire ten kids.  What if you want to focus on your career, but he’s looking for a stay-at-home wife?

You also want insight into his personal values or beliefs.  Not to mention his habits, financial goals, sore subjects, likes and dislikes, and where he pictures the relationship between you two going.

A relationship is like a house.  The deeper you let a person into your home (life), the harder it is to get them out.  For instance, if you let someone into the most intimate places in your house (life) and things don't work out, it can be emotionally draining and frustrating to get them out.  Plus, you’ll need to repair the damage and consider potentially opening up to someone new again.

While someone is still in the front room of your house (life), like a boyfriend, it's not as hurtful or draining when things don't work out. It is essential to find details out now while the knot is untied, because once the knot is tied (in marriage), it can be stressful and heartbreaking to get it undone.

Dating is the perfect time to get everything out in the open.  So, since guys aren't the easiest to get to open up, we have a fun way to get your guy to share information about himself.  It can be done without making him feel like he's in an interrogation room at a police station.

And, just like that, we’re ready to get down to business. 

175 Fun Questions to Ask Your Boyfriend to Know Him Better

Your questions can be about personal preferences and experiences to shine a light in areas of his thinking you may not have known.

  1. Which do you prefer, a home-cooked meal or dining out?
  2. Do you prefer an evening out with friends or a relaxing evening at home?
  3. If your life were a movie, what would the title be?
  4. If your life were a TV show, which actor would play you?
  5. Favorite Sunday activity you never miss, Football or Church?
  6. Which animal best describes your personality?
  7. If you were a vehicle, would you be a sports car or a pickup truck?  And why?
  8. What makes you sad?
  9. What do you find most frustrating?
  10. If you were a superhero, what would be your superpower?
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  1. If you were Superman, what would be your kryptonite?
  2. What is the best advice your mom ever gave you?
  3. What advice would you give to your 18-year-old self about life choices?
  4. What is your one big personal regret?
  5. What do you wish you were better at doing?
  6. Would you rather be on social media or at a social gathering?
  7. What would you do for a living if it were up to your dad?
  8. What is the funniest experience you’ve ever had at a family gathering?
  9. What is your favorite game to play at family gatherings?
  10. Do you prefer gardening or mowing the grass?
  11. Are you a daredevil, or do you play it safe?
  12. What is the most dangerous situation you have ever been in?
  13. How would you use your authority if you were king for a day?
  14. If you won $100 million in the lottery, what is the first thing you would buy?
  15. What is the most romantic gesture you have ever made to show your interest in someone?
  16. Name three people smarter and wiser than you?
  17. If your life were a movie, what would be your theme song?
  18. Could you stay off your cell phone for a year if it meant you would be rewarded $10 million at the end of that year?
  19. Would you go surfing on the beach or skiing in the mountains?
  20. When I say the term “Full House,” what is the first thing that comes to mind?  A house full of people, playing cards, or the TV show?
  21. What lasted longer, the movie Titanic or your last relationship?
  22. If a random stranger or your ex were hanging off the side of a building, and you could only save one of them, who would it be?
  23. How would you describe our relationship going forward, a drag race or the Indy 500?
  24. If you found a million dollars on your morning jog, what do you do with it, turn it in or keep it?
  25. If your life were a movie, what genre would it be, drama, suspense, action, or comedy?
  26. What professional team mascot best describes you when you are angry?
  27. If you were in the mafia, what would be your role, the boss, the brains, money man, or the muscle?
  28. Which best describes you, being a firefighter (hero), a police officer (protector), or an EMT (healer)?
  29. If your life were a National Holiday, which holiday would it be, Christmas, Thanksgiving, Independence Day, Valentine’s Day, etc.?
  30. If your life were a movie, what would be the rating, G, PG, PG-13, R, or something else?
  31. What is the best thing about being you?
  32. Who is the funniest person you know?
  33. Do you still dress up for Halloween?
  34. The sun is up, and you are off work for the day.  Do you stay on the couch all day or get up and get moving?
  35. If we had a spare room, would it be used for a man cave or office?
  36. Do my questions bore you?
  37. How do you keep track of information, write it down, put it in your phone, or go by memory?
  38. You've had a flat on the side of the road.  Do you call AAA or fix the flat yourself?
  39. My parents just gave me $5000, what is your reaction?
  40. Your child is struggling with math, do you help them yourself, hire a tutor, or talk to the teacher?
  41. Your child brings home a failing grade.  Are you angry with the teacher or disappointed with your child?
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  1. When putting together a complicated piece of furniture, do you read the instructions, or do you figure it out on your own?
  2. Your child needs braces, but you cannot afford them.  Do you ask for a loan or get a side hustle to pay for them?
  3. Are you more of a Batman or Robin?
  4. If you were a retail store, would you be a Wal-Mart, a sporting goods store, clothing store, electronic store, etc.?
  5. If you were a season of the year, which of the four seasons would you be?
  6. If there was one situation I could fix and you would never have to worry about it again, what would it be?
  7. If you were involved with a sports franchise, would you rather be a player on the team, the star, the coach, general manager, or the owner?
  8. What do they ask for when people call and ask you for help?
  9. What’s the last contest you entered?
  10. What is your favorite flavor of ice cream?
  11. When was the last time you laughed so hard you started crying?
  12. What kind of soda are you?  For example, Coke, Pepsi, A Diet Soda, or Fruit Flavor.
  13. What animal would you use to describe yourself before your morning coffee?
  14. If you were a video game console, which would you be?  A PlayStation, Xbox, Nintendo, Atari, Sega Genesis, etc.?
  15. If you were a vacation destination, would you be a beach, scenic landscape, mountain range, ski trip, resort, or hiking trail?
  16. You won a house in the location of your choice.  Would it be a beach house, a lake house in a secluded area, a suburban place, in the middle of the city, etc.?
  17. You're on Family Feud.  Who are you taking with you as the other four contestants?
  18. Are you a dog person, cat person, or both?
  19. If your life were a News station, would it be SportsCenter, CNN, or Local News at 10?

It is always important to dig deeper and find out as much as possible about your boyfriend before making a long-term commitment.  These questions are a creative way for you to use your imagination, while opening himself up to you simultaneously.

  1. 20/20 wants to feature you on their show.  Based on a past event, what are you going on the show to talk about?
  2. You are in a gym full of 5th graders as a guest speaker.  What advice are you giving them?
  3. If you win a million dollars today, will you still work tomorrow?
  4. If you were a schoolteacher, what subject would you teach?
  5. If you were a green vegetable, which one would you be?
  6. Who would your parents say you were if you were a cartoon character?
  7. You’re a genre of music, which one are you?
  8. If a guy has been hitting on me at work, how would you want me to handle it?
  9. Which best describes you, Spearmint Gum or Bible Gum?
  10. Which board game best describes your personality?
  11. Are you the Tortoise or the Hare?
  12. If you were a vehicle, Make and Model, what would you be?
  13. Are you cold or warm-natured?
  14. Are you a 4-wheeler or a motorcycle?
  15. If you could change anything about yourself, what would it be?
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  1. You only have $5 to spend on food for a night.  What are you buying?
  2. You see a woman hitchhiking.  Do you stop and offer her a ride?
  3. A man is hitchhiking as you drive by.  Do you offer him a ride?
  4. How do you like your eggs, sunny side up, over easy, or scrambled?
  5. If you were a steak, would you be rare, medium-rare, medium, medium-well, or well done?
  6. Do you prefer a fire in the fireplace or building a bonfire outside?
  7. You see an old man get jumped in the park by a younger guy.  Do you keep walking or go help the older gentleman?
  8. Steak on a grill in the backyard or steak from Applebee’s?
  9. Bottled water or tap water?
  10. We are driving my car, and we go to the gas station.  I’m paying for the gas, but are you pumping it for me or not?
  11. What type of chicken wings are you, hot and spicy, mild, or plain?
  12. Do you prefer the book or the movie version of a story?
  13. If you went to the Olympics, what would be your competing sport?
  14. If you were in the Circus, what would be your character?
  15. Let's say you made the Guinness book of world records.  What record did you break?
  16. If you had to grade your parents based on performance, what would their grades be?
  17. In 5 years, are you likely to buy a sports car, a house, or property?
  18. What toppings do you like on your sub sandwich?
  19. Someone cuts in front of you in traffic and slams on their brakes.  You manage to keep from hitting them.  You have children in the car with you; what is your reaction?
  20. Your neighbor is having a wild party late at night.  What is your reaction?
  21. What is the worst feeling in the world?
  22. If I robbed a store and I came to hide out at your house, would you let me stay, make me leave, or turn me in to the police?
  23. Do you prefer showers or baths?
  24. There is a mouse in your house.  Do you set a trap or call pest control?
  25. If you could meet anyone in the world, who would it be?
  26. What advice would you give him if you could see yourself from ten years ago?
  27. Which sports car do you prefer, American Muscle or Foreign Street Racer?
  28. If you were a cereal brand, what would people say you were, Fruit Loops, Raisin Bran, Captain Crunch, or Honey Nut Cheerios?
  29. If you could live in any century and decade from the past, what would it be?
  30. You have a broken leg and need to get groceries; do you use your crutches while pushing a shopping cart, or do you use an electric scooter from the store?
  31. You only have enough money to buy a Christmas present for one person in your life, for whom are you buying a gift?

You want to be with a person of integrity, right?  So ask these fun questions to delve into his perspective and see if it fits your value system.

  1. You withdraw 500 dollars from the bank teller.  You notice the teller gave you 600 dollars by mistake when you get home.  What do you do with the extra $100?
  2. An old gentleman drops a $50 bill while walking out of the grocery store but doesn’t know it.  So you pick up the 50, do you give it to him or keep it?
  3. A well-dressed businessperson drops $50 as he leaves the grocery store, but he doesn't know it.  So you pick up the 50.   Do you give it to him or keep it?
  4. You see a young man steal some items in the electronics department of a store.  Do you report him to an associate, or do you feel it’s not your problem?
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  1. Your coworkers are stealing products and tools from work.  Do you report it, or do you feel it's not your concern?
  2. Your best friend is cheating on his wife and sometimes asks you to cover for him.  What do you do about it?
  3. If you were a seasoning, which would you be, salt, garlic, Cheyenne Pepper?
  4. Can you describe me in five words?
  5. When I text you, what is the first thing that comes to mind?
  6. If I fell in a cage with a hungry lion, would you jump in to save me?

You want to take the time to learn about your boyfriend’s quirks and what makes him tick.  Gain insight into what to expect from him when things don't go as planned and see how confident he is.  Furthermore, is your guy self-centered or the kind of person who looks out for others? 

  1. What combination of foods do you eat together that most people find gross?
  2. What is the worst date you have ever been on?
  3. What is the scariest thing that has ever happened on a date?
  4. Have you ever been on a weird blind date?
  5. What would you do if you could have superhuman strength and invincibility for a day?
  6. If you could go back in history to witness any historical event, what would it be?
  7. What is the weirdest dream you ever had?
  8. If I could turn into any celebrity for a day, who would you want me to be?
  9. What was your favorite toy as a kid?
  10. Are you a night owl or up at the crack of dawn?
  11. Where can you picture the two of us in ten years?
  12. If you could take me anywhere in the world, where would you take me?
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  1. What is your favorite thing about me?
  2. What do you feel is your worst quality?
  3. What do you feel is your greatest pet peeve?
  4. What is the most spontaneous thing you have ever done?
  5. What is your favorite thing about me?
  6. Are you a hugger?
  7. What was the first thought that came to your mind when we met?
  8. What do you most admire about your parent’s relationship?
  9. If we went on a long road trip, who’s driving?
  10. What is the kindest thing you have ever done for someone?
  11. What would you wear if you could dress any way you want to for work?
  12. What type of fruit would you be if you were a piece of fruit?
  13. If you could buy me anything in the world and money was no object, what would you buy me?
  14. Are you ticklish?
  15. What kind of grades did you get in school?
  16. What do you admire most about your siblings?
  17. Who was your hero when you were a child?
  18. What is your favorite body part?
  19. Do you name your vehicles?  If so, what are their names?
  20. What is your favorite channel to watch on TV?
  21. A new iPhone is coming out.  Are you waiting in line to be the first to get it?
  22. What does your ideal weekend consist of?
  23. What is your least favorite household chore?
  24. How do you feel about public displays of affection?
  25. What have you found to be the best way to manage stress?
  26. How do you control your anger?
  27. Describe yourself in 5 words?
  28. When do you seem to second guess yourself the most?
  29. Do you think we could remain friends, if this relationship didn't work out?
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  1. Can men and women have a strictly platonic friendship?
  2. We have reservations for dinner at my favorite restaurant.  Still, your friends have front row tickets to see your favorite team play the same night, and they invite you.  So what are you going to do?
  3. I have always wanted to be a __________ (you fill in the blank with your own goals and ambitions).  What do you think about that?
  4. What is your feeling concerning marriage?
  5. A friend of mine flirts with you, do you tell me or not?
  6. How would you deal with a disagreement with one of my family members?
  7. If I were sick with a long-term illness, would you stick by me until I recover?
  8. Tell me about a time you made the best of a bad situation?

Final thoughts on 175 Fun Questions to Ask Your Boyfriend to Know Him Better.

These questions may seem a bit random; but, they are a fun and creative way to gain access to your boyfriend's way of thinking, priorities, dreams, values, goals… and how you fit into the picture.

So go, have fun with it!  You'll likely learn some amazing things with these questions to ask your boyfriend, while also hopefully avoiding any “red flags” that could lead to a potentially life changing mistake. Conversely, these questions may also help reinforce the fact that the boyfriend you have now is a keeper.

For more questions similar to these, check out our article on random questions to ask people throughout your life to get the conversation going.

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175 Fun Questions to Ask Your Boyfriend to Know Him Better