180+ Really Good Questions to Ask Your Boyfriend

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If you are looking for the best things to ask your boyfriend to know him better and to create a deeper connection between you two, then you have landed on the right place.

This list of questions is based on the fact that you two are already dating for some time.

If you have just started dating, or you just want to go on a first date with him, then this article will be much better for you – 150+ Great Questions to Ask a Guy You Like.

CUTE & ROMANTIC QUESTIONS TO ASK HIM

couple talking and laughing

1. Do I make you want a future with me?
2. What do you love about me the most?
3. Would you risk your life to save mine?
4. Do you believe in love at first sight?
5. Would you sacrifice something to keep our relationship going?
6. Do you remember the day we met?
7. Do you feel like you can tell me anything?
8. Do you believe in soulmates?
9. If you have a vision of the perfect date to take me on, what is it like?
10. Would you be my lover in the next life?
11. What was your first impression of me when we actually met?
12. Is there a song that you think of when you think of me?
13. What was the first thing that you noticed about me that made you feel attracted?
14. What are the qualities you like in me the most?
15. How special is a memory of your first love to you?
16. When did you have your first crush?
17. What is the craziest thing you can do for me?
18. What roles do love and affection play in your life?
19. Who are three people in your life that you would risk dying for?
20. Do you think your significant other can be both your best friend and your lover?
21. Would you introduce me to your parents?
22. What is a quirky thing about me that you love?
23. How would you describe our first kiss?
24. If I was scared, would you hold me?
25. Do you like kissing in the dark or kissing in the rain more?
26. When you’re alone, do you think about me?
27. Would you hold my hand in public?
28. What is your favorite dream that involved me?
29. Would you kiss me in public?
30. Does it make you smile when I send you a text message?
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QUESTIONS TO SHOW INTEREST IN HIM

woman talking to a man

1. Can you repair your own car?
2. Describe your dream house.
3. Do you like to travel?
4. Describe yourself in a single word.
5. If you could only eat one food the rest of your life, what would it be?
6. Are you close to your parents?
7. What’s your dream job?
8. Who is your favorite superhero? What would you do with his or her super-power?
9. What is your favorite rainy day movie?
10. If you’re having a bad day, how can I cheer you up?
11. What makes you smile?
12. What is that one place in the world you would like to visit at least once in your life, and why?
13. What’s your favorite sport to play or watch?
14. Have you cried at any movie?
15. What are your hobbies?
16. Do you think of yourself as being nice or naughty?
17. What is your most favorite meal?
18. Are you a morning person or night owl?
19. What’s your most favorite music genre?
20. What is your most favorite romantic activity?
21. Are you religious or spiritual?
22. What was the last book that you got so absorbed in that you couldn’t put it down?
23. What´s the best vacation you´ve ever had?
24. Are you a superstitious type of person? About what?
25. What three events made the biggest impact on who you are today?
26. How many phones have you broken or lost?
27. What´s your relationship like with your mother?
28. Do you prefer going out or staying in?
29. How many days a week do you get together with friends?
30. Is there anything you wouldn’t want your family to know?
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QUESTIONS TO MAKE HIM OPEN TO YOU

couple on a date

1. Is there anything you’ve done in the past that you can’t forgive yourself for?
2. Do you still have feelings for someone in your past?
3. Did you ever feel totally insecure about something?
4. Have you ever cheated on a girlfriend?
5. What is your biggest regret in life?
6. What’s the most embarrassing moment of your life so far?
7. What was the first thing you thought of me when you saw me?
8. If you had to choose between all the money in the world or a devoted, loving family, what would you choose?
9. What are you most afraid of?
10. When was the last time you cried?
11. Have you ever been in love?
12. What´s the most disappointed you´ve ever been?
13. Do you have a secret hunch about how you will die?
14. Have you ever had your heart broken?
15. What was your best relationship?
16. What is your worst trait?
17. Have I done anything to hurt you that you never told me about?
18. Were you ever bullied in school?
19. What´s the worst dream you´ve ever had?
20. Do you believe in marriage?
21. What movie do you wish life was more like?
22. Is there anything you’ve done in the past that you can’t forgive yourself for?
23. What do you consider to be your greatest accomplishment in life?
24. What’s your biggest fantasy?
25. Which is better to listen to – your heart or your brain?
26. Would you rather be a good guy or a bad guy in a comic/movie?
27. What childish thing do you still enjoy?
28. What was your best drop the mic moment?
29. What long shot have you taken that really paid off?
30. Who or what is your nemesis?
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THINKING ABOUT MOVING IN TOGETHER? ASK THESE FIRST

couple moving in together

1. Have you ever thought about moving in together? Do you want to in the future?
2. Do you plan to adopt or purchase a pet in the near future?
3. Would you ever consider having additional roommates to cut costs if we had a place with enough space?
4. Imagine we live together. Who will be paying for bills?
5. How will you help me keep the apartment clean?
6. What is your favorite thing to wear to bed?
7. When do you think is the best time for us to move together?
8. How often would you like to have company over?
9. What is your favorite thing to wear when you are at home?
10. If we will live together and suddenly break up, who will move out?
11. How do you like to fall asleep when I’m not there? Do you have any sleeping quirks?
12. Are you a neat freak or do you tend to have socks and other items lying around everywhere, most of the time?
13. How is your actual financial situation? Do you have any debt?
14. How will we make sure we each get to spend time alone when we share the same place?
15. What will happen if our sex life slows down?
16. How will we make sure the chores around the house are divided fairly?
17. How will we make room for alone time?
18. How long do you think we will live together before getting married?
19. What is our ultimate goal of living together?
20. Can you pay your full half of the bills on time every month?
21. How will we usually handle meals?
22. If I have to work really late, will you have a problem with cooking or picking up some dinner for both of us?
23. Are we going to have a joint checking account?
24. How will you help me take care of our pets?
25. What about our common future?
26. What is your expectation of living with me?
27. How should we handle guests?
28. Do you see us getting married in the near future?
29. What will we do if one of us lost our job?
30. Do you think we have a similar living style? 
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QUESTIONS TO ASK HIM ABOUT HIS PAST

man and woman smiling

1. When was your first kiss?
2. What’s the worst thing you’ve ever done?
3. What time in your past would you love to return to? Why?
4. What was your parents’ relationship like?
5. What are some of your favorite childhood memories?
6. Have you ever broken the law?
7. What are some prominent things that have happened in your past that you think have contributed greatly to who you are today?
8. How did your last relationship end?
9. How many sexual partners have you had?
10. What do you consider to be your greatest accomplishment in life so far?
11. If you could change anything about the way you were raised, what would it be?
12. What were you like as a child?
13. What is the craziest/weirdest thing you have ever done?
14. What is your most terrible memory?
15. When was the first time you said I love you?
16. What is a tradition you did as a child that you want to do with your kids someday?
17. Do you have any dreams from childhood that you can vividly recall?
18. What are some things in life that you had to learn the hard way?
19. What were your childhood aspirations, and how have they changed?
20. How have you changed the most since you were younger?
21. Have you ever had a wet dream?
22. What is the most courageous thing you have ever done in your life?
23. Have you ever experimented with legal/illegal drugs?
24. What’s the biggest lie you ever told—did you get busted?
25. Do you still have feelings for someone from your past?
26. How did your last relationship work out?
27. What disappointed you about your last girlfriend and led you to want to break up?
28. When did you lose your virginity? How did it happen?
29. What’s the riskiest thing you’ve done in life? Sexually?
30. What is the worst date you’ve ever been on?
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QUESTIONS TO ASK HIM ABOUT FUTURE

couple hugging each other on pier

1. Where do you see our relationship in 5 years?
2. What would you like your greatest accomplishment to be?
3. What are your thoughts on marriage?
4. How important are children to you?
5. What do you want to have going on in your life in 5 years, or 10, or 15?
6. If money were no object, where would you want to live?
7. What is your idea of a perfect honeymoon spot?
8. How many kids do you want to have in the future?
9. What do you want to do before and experience before you die?
10. What Fictional world would you like to live in?
11. What would you do if I got pregnant?
12. Where is our relationship going?
13. What are some of your goals in life?
14. What do you think of being forever together?
15. Do you see us getting married in the future?
16. When you die, do you want to be buried or cremated? Why?
17. Are you looking for a serious commitment in near future?
18. Do you see me in your future?
19. Would you ever consider moving in together?
20. What do you most fear about getting older?
21. What serious goal do you want to accomplish in your lifetime the most?
22. How will we spend our holidays?
23. What fun goal do you feel you must do before you die?
24. What are your thoughts on how to discipline children?
25. When you die, what part of your personality do you want to be remembered for?
26. Would you ever consider moving in together?
27. What will be the world like in 25 years?
28. What are your retirement plans?
29. What crazy activities do you dream of trying someday?
30. If we were married and my career forced me to move, would you come with me?
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FUNNY QUESTIONS TO MAKE HIM LAUGH

couple talking and drinking coffee

1. Is there anything you wouldn’t do for 10 million dollars?
2. What career did you want to have when you were in kindergarten?
3. What was your worst vacation ever?
4. What toy from your childhood was really creepy?
5. What is the craziest thing you have done?
6. What nickname would you give me based off my personality or a body part?
7. Will you tell me if I have lipstick on my teeth or if my hair is standing straight up?
8. What is your favorite board game?
9. What’s the weirdest thing you’ve ever eaten and liked?
10. If we were in a group at a party, and I told a horrible joke that no one else laughed at, what would you do?
11. If you made up an ice cream flavor, what would be in it?
12. When your dog farts, do you leave the room or tough it out?
13. Have you ever look in the mirror and wink at yourself?
14. What’s more gross: Yellow teeth or yellow toenails/fingernails?
15. Has anyone ever walked in on you sitting on the toilet?
16. If you had to kiss a guy other than family, who would it be?
17. Have you ever peed in a pool?
18. What would be your weapon of choice in a zombie apocalypse?
19. What’s the grossest thing you’ve ever eaten?
20. Would you rather crank call or ding-dong-ditch your neighbor?
21. Do you know how to spell antidisestablishmentarianism?
22. If you had a pet unicorn, what would you name it?
23. Has anyone ever walked in on you in the bathroom?
24. Who was your celebrity crush as a teen?
25. Finish this statement: “Look out! It’s a _____!”
26. What’s the worst movie you’ve ever paid to see?
27. When you were a kid, what did you think being this age would be like?
28. Kill, screw, or marry: Miss Piggy, the flying dog from Never Ending Story, or Tweetie bird?
29. What was your childhood nickname?
30. If you could give your bunny a super power of some kind, what would it be?
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DEEP THOUGH-PROVOKING QUESTIONS

1. What would you change about your life if you knew you would never die?
2. Does truth exist without evidence? Without proof of something, can it really be considered a truth?
3. What is the honor, and does it even matter anymore?
4. If you had a year left to live, what would you achieve over the next 12 months?
5. If you could send a message to the entire world, what would you say in 30 seconds?
6. How many people do you truly love? What are you doing for them?
7. Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?
8. What have you done to pursue your dreams lately? How about today?
9. How do you apply the learning from your past mistakes to your actions today?
10. Is being open-minded a virtue, if it’s causing destructive ideas to spread throughout society?
11. When things break, do you prefer to fix them or replace them?
12. What would you want to be said about you after you die?
13. Do you believe there is good in everyone?
14. Do you forgive and forget or forgive and remember?
15. If you were told you have a terminal illness, how would you take the news?
16. Do you think there is an afterlife?
17. If a crystal ball could tell you the truth about your life, me, or the future, what would you want to know?
18. What is one area in your life where you feel like something is missing?
19. Would you sacrifice yourself for a stranger?
20. What part about the future scares you?
21. If you died tonight, is there anything you’d regret not having told someone?
22. Do you believe there’s one person you’re ‘meant’ to be with?
23. Is life anything like you had pictured it would be growing up?
24. What’s one thing you think makes our relationship unique from everyone else’s?
25. What is the most worthwhile goal a person can dedicate their life to?
26. What’s one thing about your life you would never change for someone else, including me?
27. What do you consider a wasted life?
28. What’s the biggest struggle that you’ve ever faced?
29. What stops people from understanding themselves?
30. Do you think your significant other can be both your best friend and your lover?
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MOST INTIMATE QUESTIONS ABOUT HIS LOVE LIFE

couple on first date

1. Do you like it when I take control in bed or do you like being in control?
2. Of all the things I’ve done with you in the bedroom, what’s your favorite?
3. What is your favorite part of my body?
4. Have you ever had sex in a public place?
5. Try to guess – what’s the color of my underwear right now?
6. When was the last time I was in one of your dreams?
7. Have you read 50 Shades Of Grey? If so, did it turn you on?
8. What is your biggest turn on?
9. Do you like it when I’m the dominant one in bed or do you prefer leading things?
10. Do you sleep in pajamas, underwear or nothing at all?
11. What’s the one thing I do that turns you on the most?
12. How often do you think couples should make love?
13. Have you ever taken naked pictures of yourself?
14. Do you get jealous when other guys check me out?
15. How do you feel about pornography?
16. How often do guys really think about doing it?
17. Is laughing in the bedroom okay with you or do you prefer keeping things serious?
18. You decide to give me a full body massage, where do you start?
19. Do you own any sex toys?
20. How can we make our sex life better?
21. What do you think of open relationships?
22. What was your first “adult” experience?
23. Have you ever had a one night stand?
24. Have you ever done it in a movie theater?
25. What do you think about dirty talk over the phone or Facetime?
26. What attempts did you make to woo me? Which ones worked?
27. Do you like it with the lights on or off?
28. Do you like experimenting with different positions?
29. Where is the most public place that you’ve touched yourself?
30. Has anyone accidentally seen you naked?
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THINKING ABOUT GETTING ENGAGED? ASK THESE FIRST

wedding image

1. What are your retirement plans?
2. How important is a religion? How will we celebrate religious holidays, if at all?
3. Do you have any bad spending habits? How about financial debts?
4. Do you like my parents? What do you think about them?
5. Where do you want to live in the long term?
6. Have you fully disclosed to me your health history, both physical and mental?
7. Do you want to have kids? If so, then how many?
8. Will you support my decision if I want to go back to school one day?
9. What are your thoughts on how to raise and discipline children?
10. How will we handle our in-laws?
11. How will we spend our holidays when we will have children?
12. Do you want a small wedding, a large one, a visit to the courthouse, an elopement, or do you have no opinion at all?
13. What kind of dad do you want to be?
14. How far should we take flirting with other people? Is watching pornography O.K.?
15. If I got really sick with a long-term illness, would you stick around to take care of me?
16. How do you see us 10 years from now?
17. What do you think each person’s role is in a marriage?
18. What do you think is the best way to handle disagreements in a marriage?
19. Are you a spender or a saver?
20. What is your stance on divorce?
21. What does my family do that annoys you?
22. Would you be agreeable to staying home with the kids if my career was about to take off or if I made enough at my job to support that arrangement?
23. If I have a disagreement with one of your family members or friends, will you stand up for me?
24. What’s your take on getting the housework done if both partners work outside the home?
25. Do you think that prenatal tests for certain birth defects or disorders should be done? How would you react to bad news?
26. Are you satisfied emotionally and sexually in the relationship?
27. How do you feel about taking in family members during a hard time? Elderly parents?
28. How would you feel about me going on a trip with the girls for a couple of weeks?
29. Are you open to the idea of marriage counseling if we would have problems?
30. Did your family throw plates, calmly discuss issues or silently shut down when disagreements arose?
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DIRTY QUESTIONS TO KNOW HOW KINKY HE IS

couple having sex black white

1. How would you describe your package?
2. Ever try using a sex toy during sex?
3. I drip hot wax onto your chest unexpectedly, how do you react?
4. Do you think you could get me off just by kissing me and touching my breasts? Want to try?
5. Where is the strangest place you’ve ever had sex?
6. Are you quiet, or do you like to make a lot of noise?
7. Do you like your hair pulled?
8. So imagine you can only have one type of sex for the rest of your life – oral, anal, or regular. Which one do you pick?
9. Have you ever had sex with one girl and then had sex with another on the same day? Did they know about each other?
10. Have you ever had a one night stand?
11. What is your favorite thing I do to you in bed?
12. Do you prefer top or bottom?
13. Have you ever been caught going solo? By who?
14. Do you like when I send you dirty pictures?
15. Do you prefer having some fun in the morning or at night?
16. Under the sheets, are you Iron Man, The Hulk, Thor, or Captain America?
17. How many rounds do you think you could go in one night? What about on our wedding night?
18. Do you like playing rough?
19. What’s the longest you’ve gone without doing it?
20. Do you like it when I go down on you?
21. If I could only wear yoga pants or short skirts for the rest of my life, what would you choose for me?
22. Do you like watching me touch myself?
23. What’s your favorite thing to do to me?
24. Have you ever woken up beside someone you regretted sleeping with?
25. Do you want to know what I’m wearing?
26. Hair down there or all bare?
27. What’s more important … boobs or butt?
28. Would you be angry if you saw me making out with a really hot girl?
29. Have you ever woken the neighbors because you were so loud in the bedroom?
30. What’s the naughtiest thing you’ve ever done?
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Hey folks! My pen name is James Buzinko (a.k.a. Stallion) and I want to make this THE GREATEST place for every guy to master the arts of love, dating and attraction! I am young, free and my motto is "Carpe Diem".