90+ Really Good Questions to Ask Your Boyfriend

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 – 21+ Great Questions to Ask a Guy You Like.

Top 10 Cute & Romantic Questions
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?
10 Best Questions to Show Your Interest in Him

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?
Top 10 Questions to Make Him Open to You

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?
10 Best Questions to Ask About His Past

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?
Top 10 Questions About Future

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 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?
10 Best Funny Questions to Ask Him

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?
Top 10 Deep & Intriguing Questions That Provoke Thoughts

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?
10 Most Intimate Questions

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?
Top 10 Dirty Questions to Spice up Your Relationship

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?

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