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Freaky Questions to Ask Your Boyfriend – A Fun Guide

Freaky Questions to Ask Your Boyfriend – A Fun Guide

Updated on Nov 07, 2023

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

200+ Freaky Questions to Ask Your Boyfriend - A Fun Guide

Are you trying to maintain that spark in your relationship? Do you want to experience that newness like a new relationship? Get ready for a whirlwind of questions that will make your dates more romantic, and your texts more exciting!

This set of freaky questions to ask your boyfriend will help you to keep the flame of your love alive. 

In this guide, you will find all the types of questions you may wish to ask your boy in different scenarios. Get ready to download some amazing questions to ask your boy and add different shades of love to your relationship. 

200+ Freaky Questions to Ask Your Boyfriend - A Fun Guide
200+ Freaky Questions to Ask Your Boyfriend – A Fun Guide

Freaky questions to ask your boyfriend over text

Texts can be boring sometimes but when you know how to spice up your conversation with your boy then texts can be so much fun. This list of sexy questions will help you to take the conversation to the next level and keep them going all day and night. 

You will enjoy every bit with your friend with the help of these questions. 

  1. Do you keep in touch with your ex-partners?
  2. Has there ever been a time when you cheated on me?
  3. What are your deepest fears about us?
  4. Touching myself while looking at your pictures is my favorite thing to do. Are you able to send me one right now? Or would it be better to visit me in person? 
  5. Who would you choose if you could have one girl in the world?
  6. Are you more of a boobs or a butt guy?
  7. Would you rather give or receive?
  8. What do you think about adult movies?
  9. Are there any places that you especially like to be touched?
  10. If you could be kissed anywhere, where would it be?
  11. The best physical feature of yours, according to you?
  12. Would you do anything for me right now if I asked?
  13. Would you ever consider ripping my clothes off?
  14. Is there anything you want to tell me about your dirty dreams?
  15. Is it more convenient to talk dirty on the phone or over Facetime?
  16. Is friendship with benefits something you would consider?
  17. In what way is making love different from sex?
  18. Is your ideal time for intimacy the late evening hours or the early morning hours?
  19. Are you familiar with the concept of nudist beaches?
  20. How many times have you been caught in the act? 
  21. What dirty pictures have you got on your phone?
  22. Would you be interested in seeing me touch my body?

Freaky sex questions to ask your boyfriend

You can easily turn on your partner by using some fun and exciting questions or hints . Use these seductively sexy questions to spice up your conversation and enjoy your time together even more!

  1. In regards to your love life, what is your freakiest fantasy?
  2. When you go to bed, what do you wear?
  3. Do you mind taking a shirtless selfie with me beside a mirror?
  4. When I am walking away, how often do you check me out?
  5. What are your wild thoughts about close relatives?
  6. Do you enjoy it when a lady massages your body?
  7. What is your experience with one-night stands?
  8. When you were a teenager doing your first kiss, how did you feel?
  9. I’m not wearing my underwear. Would you like to come over? 
  10. Is there anything you would like to do to me that is dirty? Can you tell me how you would like me to treat you?
  11. If I said I can’t avoid thinking of you at night when I can’t stand not touching myself? What would you think of that? 
  12. If you had a chance to kiss me right now, where would you want to kiss me? – 
  13. Would you prefer to start with the upper or lower part of my body if we were lying in bed now? 
  14. I want you to rip my clothes off. What are your chances of doing that with your teeth? 
  15. The whole time I’m with you, I’m laughing. Have you noticed? 
  16. Would you like to guess what colour my new lingerie is? 
  17. Do you know how wonderful your tongue is? – Lісkіng іѕ hіѕ ѕресіаltу.
  18. What pose would you want if you could order a picture of me right now? 
  19. How about coming over? Now that my boobs are out, I would love it if you touched my body. 
  20. If you were to bind me, would you prefer blindfolding me or tying me up?
  21. Could you imagine how you would feel if I served you breakfast by wearing nothing but an apron? We can test it out if you come over. 
  22. In your opinion, what makes a lady sexy? Do I do well?

Good freaky questions to ask

Talking about fun, romantic, and light topics never hurts. Ask your boyfriend some good questions to create some joyful memories with this list of good freaky questions. And don’t forget to add your own touch to get more close to him.  

  1. How often do you flirt with your best friend’s girlfriend?
  2. How often do you watch adult content prior to making out?
  3. Do you know how to play Cards Against Humanity?
  4. What was the first time you realized you loved/liked me?
  5. How do you feel when you wake up next to me in the morning?
  6. How would you like to spend our honeymoon if we get married?
  7. How about writing a song for me someday?
  8. Do you think you could write a poem about me one day?
  9. There is always a reason for everything-why did we meet?
  10. Is there anything you remember from the first time you met me that sticks out in your mind?
  11. How does it make you feel when I text you?
  12. Is it embarrassing to you if I call you a pet name before your friends?’
  13. What would you say or do if you saw another man trying to pick you up?
  14. How would you describe the perfect date you would take me on if you had one
  15. Could you please spell antidisestablishmentarianism for me?
  16. What is your daily selfie count? Are you going to delete them or keep them?
  17. Is there anything you love but would hate if it was a Dairy Queen Blizzard?
  18. What’s the first food that comes to mind when you think of a birthday?
  19. Which nickname would you choose if you were a biker?
  20. What is the most efficient mode of transportation?
  21. Do you have the cheesiest pick up line you’ve ever used while meeting a girl? Was it successful?
  22. Can you recall a time when you were ejected from a public place?
  23. Do you have a favorite chick flick?
  24. Which of my non-physical qualities do you like most?

Freaky questions when your bored

Are you getting bored? Make your time fly away by asking your boyfriend some weird questions that will make your time fly quickly. Using this list you will be able to keep your conversation going with questions of all types, such as fun, romantic, and creative. 

  1. Do you realize that you make me vеry happy? 
  2. Why do I fall in love with you every day? 
  3. At what point in our relationship do you feel most enthusiastic? 
  4. Is it possible to imagine the future without you? 
  5. When we aren’t together, what will you miss most about me and us? 
  6. What did you enjoy most when we were together? 
  7. Can you tell me your favorite way of holding me close? There’s nothing better than being in love, is there?
  8. Can we find a future where you are always smiling as you are now? 
  9. Would you like to relive any moments of our relationship? – Great way to recall the moments of your relationship! 
  10. What makes the perfect woman? What makes the perfect man? How would you describe their attributes? 
  11. WhIs there any reason you would break up with me?
  12. What wоuld you do if you were told that I have a deadly disease?  How will you handle the situation?  Are you still going to love me?
  13. How would you describe your ideal date night? How would you like to have spent your time in bed?

Flirty freaky questions to ask

Are you trying to make him think of you? How about some freaky flirtation with your boy. Here are a few freaky flirty questions that will help you establish good eye contact, which will make your date or conversation much more exciting.

Spice it up with your own touch to the questions and make it even sexier!

  1. The part of my body that you like the most?
  2. When I аsk you to give me my full body massage, what part would you start with?
  3. How would you have me style my hair if you dressed me up for a real-life date?
  4. Do you prefer long or short hair?
  5. Which would you consider to be your preferred style of garment: things, shorts, or a different kind?
  6. One day, I was completely exhausted upon arriving home from work. What can you do to help me relax? What would you recommend I do first?
  7. Which part of my body do you think is the most beautiful?
  8. Ever feel strange when you see another guy checking me out?
  9. Is there anything I could do to be more receptive to you?
  10. Does it make you feel good when I am talking to you or thinking about you?
  11. Do you like dirty talk? What would be a good example for me?
  12. What would you like to see me wearing (or not wearing) if you could see me wearing anything?
  13. Is it ever possible for you to make me breakfast in bed?
  14. Do you believe that we were in love right away when we met? What do you think about love at first sight?
  15. Would you find it more attractive if I wore a flirty dress or if I wore a tight top?
  16. Which would you prefer, that I wear a long shirt or that I do not wear anything at all?
  17. Is there ever a time when you brag about me to your friends?
  18. What made you turn on the most?
  19. What words would you use to describe my body in three words, if you had to use them?
  20. Is there anything you want to know about my outfit?

Funny freaky questions

Are you enchanted by his smile? No doubt about it, you love it.  This is a list of some funny freaky questions that will make your boyfriend and you laugh out loud and discuss some interesting topics you would not normally discuss with each other. 

  1. What’s happening here? Is it hot, or are we just crazy?
  2. Cute pants Is it possible for me to try the zipper?
  3. Would you mind helping me burn calories by kissing me?
  4. Would it be okay if I slept in your bed? My bed broke.
  5. What kind of camera are you? Seeing you brings a smile to my face every time.
  6. What is your name, Google? I came to you because you are the answer to everything I have been searching for.
  7. Can you tell me your name is WiFi? Perhaps there is a connection between us?
  8. Do you have a profession aside from being desirable?
  9. Is it possible for me to be quarantined with you? It’s the new ‘2021’ (flirting).
  10. Getting on Santa’s naughty list and getting dragged around under the mistletoe in this holiday edition.
  11. What do you think of The Hulk? It’s because I’m hoping you’ll crush it!
  12. Does my body look like snow? You must plough, because I am counting on you!
  13. Is it okay if I borrow a kiss? I promise I’ll return it!
  14. When we first started dating, what did you think was the funniest moment?

Random freaky questions

The best questions to ask your boyfriend are random freaky ones. This type of question includes all types of questions and is best used when you have nothing specific to ask. Feel free to ask anything and everything you want. Find something new and fun in the randomness. 

  1. How vulnerable do you think I have been in our relationship?
  2. Is there anything I do that you find absolutely beautiful about me that I see as a flaw?
  3. What is a secret you want to share with me that you haven’t yet revealed?
  4. What do you consider to be the ‘right’ person for you?
  5. What do you think of me as a ‘right’ match for you? Why am I the “right” person? (If yes) What is it about me?
  6. What fictional character are you crushing on?
  7. Do you have any experience inventing things?
  8. What name would you choose for yourself  if you could change it to anything?
  9. Would you date other people if I said you could?
  10. In your opinion, what is the most attractive attribute about you?
  11. How do you show affection to someone you love?
  12. Do you prefer to receive affection in a certain way?
  13. Is there anything special about our relationship that sets it apart from others?
  14. One thing that you could alter about our relationship, if you had the chance?
  15. Which place would you like to visit with me right now?
  16. What do you consider to be your greatest strength in this relationship?
  17. In this relationship, what is your biggest weakness?
  18. Upon first meeting me, what were your initial thoughts?
  19. When we met for the first time, what are your most memorable memories?
  20. You’re scared of love, aren’t you? 
  21. Did you create anything recently?
  22. Do you think you can survive in a jungle for a month? 
  23. What are your least favorite apps on your phone? 
  24. What has been your favorite place so far?
  25. What are you thinking right now? Answer it without thinking much. 

Relationship freaky questions

Relationships are a whole different world where you live with your partner. It is amazing how

much you can learn about each other. You can use these relationship questions to really get to know your boyfriend and deepen your relationship with him. Here we go!

  1. What is one difference between us that you absolutely adore?
  2. Which is the sexiest outfit a partner can wear?
  3. Which song do you enjoy listening to the most?
  4. Is there anything we have in common you absolutely adore?
  5. Is there something about me that makes you love me more?
  6. How does our relationship make you feel happy?
  7. Do you remember sleeping with an animal when you were a child?
  8. Are there any sounds that you love?
  9. Can you tell me what your favorite scents are?
  10. Among your favorite karaoke songs, which one is your favorite?
  11. On a rainy day, what is your favorite thing to do?
  12. Is there anything you would like us to do together that we haven’t done before?
  13. What if, for some reason, I had to move a long distance away? Would you consider working long-distance with me? Do we stay together or go our separate ways?
  14. How would you like to spend your time with me in your favorite place?
  15. Would you mind telling me one thing you are afraid to ask me but desperately want the answer to?
  16. Which of my physical characteristics do you like the most?
  17. Which particular aspect of our relationship would you miss the most if our relationships ended?
  18. How many tattoos or birthmarks do you have?
  19. What would you like me to call you when we are alone?
  20. During the beginning of our relationship, what did you think would be the length of our relationship?
  21. What one word would you use to describe our relationship?
  22. In terms of this relationship, what is your biggest fear?
  23. Does someone in particular have a special place in your heart?
  24. Are you a believer in fate? Does destiny exist?
  25. What is your flirting style? How do you usually go about it?
  26. Is there anything weird that makes you happy? 
  27. When it comes to dating, what do you like best? 
  28. What is your opinion of how we fight?
  29. Is there a chance that I might appear in your dreams and fantasies?
  30. Are we having enough sex?

Weird freaky questions

Have you ever considered having a unicorn as a pet? If not, you can ask your boyfriend these types of strange questions to see how he will respond. That sounds interesting. Right? Now let’s get started with the list of weirdly freaky questions to ask your boyfriend. 

  1. Would you make an interesting cartoon character?
  2. Can you imagine yourself as a hologram or as a two-dimensional image?
  3. Nachos. Could you tell us what you would put on yours?
  4. How would you spend five dollars at the dollar store if you had any choice?
  5. Write three random things you have experienced. Don’t hesitate!
  6. Which three things are essential to your existence?
  7. Was there anything you expected as a kid about being 40 years old?
  8. Is there anything you’ve ever eaten that was gross?
  9. Which of these things do you love, but others find disgusting?
  10. When was the last time you ate something exotic?
  11. When I say “Bruce Jenner,” what does your mind immediately begin to wander?
  12. How would you use magic if you could perform any kind of magic?
  13. Finish this sentence: “Look out! There’s a _____!”
  14. Would you do anything if you had the ability to disappear for a day?
  15. If you were given the choice, which superpower would you choose?
  16. In your opinion, which organ is the best?
  17. How did you envision yourself when you were a child?
  18. Has it ever occurred to you to pretend to be a woman?
  19. How about wearing a dress?
  20. Do you know how it feels to walk in heels?
  21. Is there a favorite dream you can remember that was funny?
  22. Have you ever experienced a nightmare that you can recall?
  23. Can you make me the best animal sounds you can?
  24. Do you know about skinny dipping?
  25. Which was your favorite item of clothing when you were a child?
  26. If your neighbor prank calls you, would you rather dump him or her?
  27. Have you ever winked at yourself while looking into a mirror?
  28. How do you feel when you indulge in something that you shouldn’t?
  29. Which is grosser, yellow teeth or yellow toenails/fingernails?
  30. Which is the one food you simply cannot give up?
  31. If you had a pet unicorn, what would you name it? or if you could make any animal your pet, what would it be and why?
  32. In what kind of ice cream flavor would you put sugar and vanilla? What do you call it?
  33. You will only be able to eat one thing until the end of your life. Which foods are you most likely to eat and why?
  34. When you were bored, did you ever watch the most awful children’s show on television?
  35. Is there a movie you’ve paid to see that’s the worst you’ve ever attended?
  36. Which of these actors are most like you: Michael Scott, Dwight Shrute, Andy Dwyer, or Ron Swanson?
  37. What would you prefer: killing Miss Piggy, screwing the flying dog from Never Ending Story, or marrying Tweety Bird?
  38. Have you ever peed in a pool?
  39. When was the last time you peed in the shower?
  40. Is there a name you would give a fluffy bunny?
  41. What would be your bunny’s super power, if you could give it one?

Freaky questions to ask your boyfriend while playing crazy tricks 

Using these crazy trips, you can add a different flavor to your conversation and make it more fun and entertaining! Adding your own flair can always make it unique. 

1. Smile 

When a person has a smile on their face, they appear more attractive and likeable. 

Smiles convey a lot about how you feel about someone. Thus, maintaining a positive and friendly facial expression will help to enhance and strengthen your connection even further. 

2. Eye Contact 

Making eye contact with him is one of the best ways to show your interest in him. If you are making prolonged eye contact, it indicates that you are interested in him. 

It’s a great way to convey your feelings without saying anything. 

3. Ask for help 

Helping each other out is the easiest and yet most effective way to get to know each other. You can call him or ask him to come over to help you move, assist you in some work or anything else that will allow you to spend time together. 

4. Compliment 

Compliments are not just for girls. Boys love to receive them as well and they make them feel special. Who doesn’t want to feel special? You can compliment him for his fashion sense, his talking style, and  behavior. 

It shows that you really care about talking to him.  

5. Use name 

By using the name of your boy repeatedly you are automatically gaining his attention and conveying respect and importance. This will make him more involved in the conversation. 

6. Show your Interest

Ask about his hobbies, interests, favorite music, and movies if you want to learn more about him. It may be a good idea to drop some subtle hints to let him know that you are interested or enjoying the conversation. 

Over to you…

Having the complete list of questions with a few tricks at your disposal can make dating and conversation more interesting. 

In this guide, all possible questions  are covered according to the different types of situations. Use it accordingly and make your conversations more interesting and fun. 

Enjoy yourself and build good relationships!

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