180+ Really Good Questions to Ask Your Boyfriend

cute couple on a date
You are looking for the best questions you can ask your boyfriend to know him better, and to create a deeper connection between you two, then you have landed on the right place.

Below, you can find over ninety questions from following categories:

  • Cute and romantic
  • Showing your interest in him
  • Making him open to you more
  • About his past
  • About his future
  • Funny
  • Deep and thought provoking
  • Intimate
  • Dirty

Keep in mind: 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.

Top 20 Cute & Romantic Questions

romatic questions to ask a guy

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 a memory of your first love is 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?

20 Best Questions to Show Your Interest in Him

couple talking about life
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?

Top 20 Questions to Make Him Open to You

discussion about life and future
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?

20 Best Questions to Ask About His Past

friends on beach talking to each other
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?

Top 20 Questions About Future

couple in love 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?

20 Best Funny Questions to Ask Him

funny couple on a cofee break
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?

Top 20 Deep & Intriguing Questions That Provoke Thoughts

discussion about deep meanings of life
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?

20 Most Intimate Questions

couple talking intimately
1. Do you like it when I take control in bed or do you like being in control?
2. Do you prefer if I shave, trim, or let it grow down there?
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. Which is more important to you – boobs or butt?
8. What is your biggest turn on?
9. Would it make you upset if you saw me making out with a really hot woman?
10. What’s the dirtiest thing you’ve ever done with someone?
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?

Top 20 Dirty Questions to Spice up Your Relationship

sexy couple talking about dirty things
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?
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Hey folks! I am James (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".