250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

By: Naveen B

As humans, we are wired to crave connections with others.

We seek out relationships with family, friends, and romantic partners as a way to fulfill this innate desire for connection.

In romantic relationships, communication plays a crucial role in building and maintaining that connection. And what better way to get to know your partner on a deeper level than through asking questions?

As the famous psychologist Carl Rogers once said, “What is most personal is most universal.” This means that the more we reveal about ourselves, the more we connect with others. And asking questions is a powerful tool for uncovering those personal details.

In this age of technology, text messaging has become a ubiquitous form of communication, and asking questions over text has become an easy way to connect with our romantic partners.

That’s why we’ve compiled a list of 250 questions to ask your boyfriend over text. These questions range from deep and thought-provoking to flirty and playful, and even to the awkward and uncomfortable.

But why is asking these questions important? Well, for starters, it allows us to understand our partners on a deeper level. By asking questions, we can learn about their values, beliefs, hopes, and dreams.

It also helps to build trust and intimacy in the relationship, as both partners feel comfortable enough to open up and share their thoughts and feelings.

So, whether you’re looking to spice up your texting conversations or deepen your connection with your partner, these questions are sure to spark some interesting conversations.

Get ready to dive deep, get juicy, and maybe even a little dirty, as we explore 250 questions to ask your boyfriend over text.

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250 Questions to ask your boyfriend over text

The following is a list of questions to ask your boyfriend over text:

1. What do you think is the most important quality in a relationship?

2. How do you typically cope with stress or anxiety?

3. What is one of your fondest childhood memories?

4. Have you ever traveled alone? If so, where did you go and what was it like?

5. What is something you’ve always wanted to learn or try but haven’t had the chance to yet?

6. What is your biggest fear and how do you manage it?

7. Do you prefer to spend your free time alone or with others?

8. What are your thoughts on marriage and starting a family?

9. What is one thing that always makes you feel better when you’re feeling down?

10. What is your favorite thing to do on a lazy day?

11. If you could live anywhere in the world, where would you choose and why?

12. How do you like to show affection or love to those close to you?

13. Have you ever experienced a major life change? How did you handle it?

14. What is your favorite way to spend a date night?

15. Do you believe in fate or do you think we have control over our own destiny?

16. What is one of your proudest accomplishments?

17. How do you balance work or school with your personal life?

18. What is your favorite type of music and why?

19. Do you have any pets or would you like to have one in the future?

20. What is something that you’ve learned recently that has impacted your life in a positive way?

Also read: 300+ Questions to ask your boyfriend from funny to deep; cute to juicy (the only list you need)

Deep questions to ask your boyfriend over text about yourself

These are some deep questions to ask your boyfriend over text about yourself:

1. What do you think is the one thing I’m most passionate about in life?

2. If you could describe my personality in one word, what would it be and why?

3. What do you think is my greatest strength, and how has it helped me in life?

4. What is the biggest challenge I’ve faced in my life so far, and how did I overcome it?

5. How do you think my childhood experiences have shaped who I am today?

6. What do you think are my core values, and how do they guide my decisions and actions?

7. What do you think is the most important lesson I’ve learned in life so far?

8. If I could change one thing about the world, what would it be, and why?

9. How do you think I handle adversity and setbacks in life?

10. What do you think is my biggest fear, and how does it affect me?

11. If I could have any career in the world, what do you think it would be, and why?

12. How do you think my upbringing and cultural background have influenced me?

13. What do you think is my greatest accomplishment, and why?

14. If I could have any superpower, what would it be, and how would I use it?

15. How do you think my experiences with love and relationships have shaped me?

Also read: 100 Questions to ask your boyfriend to get to know him (Deep, cute, romantic, funny, Interesting)

16. What do you think is the most beautiful thing about me, inside and out?

17. If I could spend a day with any historical figure, who do you think I would choose, and why?

18. What do you think is my biggest strength in relationships, and how does it benefit us as a couple?

19. How do you think my worldview and beliefs have evolved over time?

20. If I could travel anywhere in the world, where do you think I would go, and why?

21. What do you think is my greatest vulnerability, and how can I overcome it?

22. How do you think my past experiences with trauma or adversity have affected me?

23. What do you think is my biggest dream, and how can I make it a reality?

24. If I could only achieve one thing in life, what would it be, and why?

25. How do you think I approach decision-making, and what are my strengths and weaknesses in this area?

Also read: 200 Random questions to ask your boyfriend from funny to serious; flirty to deep

Weird questions to ask your boyfriend over text when bored

Here are some questions to ask your boyfriend over text when bored:

1. Have you ever experienced something supernatural or paranormal?

2. If you had to spend a night in a haunted house, who would you want to be with?

3. What’s the scariest dream you’ve ever had?

4. Have you ever had a premonition or a gut feeling that something bad was going to happen?

5. Do you believe in aliens or extraterrestrial life?

6. Have you ever been in a situation where you thought you might die?

7. If you could choose how you die, what would you choose?

8. Do you think there’s such a thing as a “perfect murder”?

9. Have you ever seen a ghost or had a paranormal encounter?

10. Do you believe in reincarnation or life after death?

11. If you could bring one person back from the dead, who would it be?

12. Have you ever had a déjà vu experience that felt too real?

13. Do you believe in curses or hexes?

14. Have you ever played with a Ouija board or attempted to communicate with the dead?

15. If you were a ghost, where would you haunt?

16. Do you think there’s such a thing as a cursed object?

17. Have you ever had a recurring nightmare?

18. If you could choose to have a superpower, but it came with a creepy side effect, would you still choose it?

19. Do you believe in the existence of monsters or mythical creatures?

20. If you found out that you were living in a simulation, how would you react?

Also read: 100 Weird questions to ask your boyfriend

freaky questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Freaky questions to ask your boyfriend over text

These are a few freaky questions to ask your boyfriend over text:

1. Do you like it when I’m naughty?

2. What’s the craziest thing you have ever done with me?

3. Have you ever done something that you regret?

4. If you could do anything to me right now, what would it be?

5. Do you ever fantasize about me?

6. What is something that you find incredibly sexy?

7. Are you willing to do something daring with me?

8. How far would you go to make me happy?

9. What is something that you would never do for me?

10. What would you do to show me how much you love me?

11. Do you ever think about doing something outrageous with me?

12. How far would you go to prove your love for me?

13. What do you find most attractive about me?

14. Are you willing to take risks for me?

15. What kind of surprises do you enjoy?

16. If I asked you to do something wild, would you do it?

17. If I asked you to do something you’ve never done before, would you do it?

18. What do you think I should do to make our relationship more exciting?

19. How do you feel when I do something unexpected?

20. What would you do to take our relationship to the next level?

funny questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)
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Funny questions to ask your boyfriend over text

Here is a list of some more Fun questions to ask your boyfriend over text (funny edition):

1. If you were a vegetable, which one would you be and why?

2. If you had to choose between giving up pizza or giving up beer, which would it be?

3. What’s the craziest thing you’ve ever done for love? (Hopefully it wasn’t too crazy)

4. Do you think you could survive a day without your phone? (I have my doubts)

5. If you could be any fictional character, who would you choose and why?

6. Would you rather fight one horse-sized duck or 100 duck-sized horses? (I’m curious about your strategy)

7. If you could only eat one food for the rest of your life, what would it be? (Hopefully it’s not something weird)

8. Have you ever accidentally sent a text to the wrong person? (I won’t judge, it’s happened to the best of us)

9. If you could only watch one movie for the rest of your life, what would it be? (Don’t worry, I won’t make you watch it over and over)

10. If you had a warning label, what would it say? (I’m sure it’s something hilarious)

11. If you were stranded on a deserted island, what three things would you bring with you? (Other than me, of course)

12. If you could switch lives with any celebrity for a day, who would it be and why? (I promise I won’t get jealous)

13. If you could only listen to one song for the rest of your life, what would it be? (Hopefully it’s not Baby Shark)

14. Do you think dogs have a secret language that humans can’t understand? (I’m convinced they do)

15. If you could be any animal for a day, which one would you choose and why? (I can’t wait to see you strut like a flamingo)

16. If you could be invisible for a day, what would you do? (Just remember, no peeking)

17. If you could only wear one color for the rest of your life, what would it be? (Hopefully it’s not neon green)

18. What’s the worst pickup line you’ve ever used? (Don’t worry, I won’t judge)

19. If you had a theme song, what would it be? (I’m sure it’s something epic)

20. If you could be any cartoon character, who would you choose and why? (I’m excited to see your inner child come out)

juicy questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Juicy questions to ask your boyfriend over text

Here are some juicy questions to ask your boyfriend over text:

1. What’s the craziest thing you’ve ever done in your life?

2. Have you ever had a crush on a friend’s girlfriend?

3. What’s the wildest party you’ve ever been to?

4. Have you ever cheated on a girlfriend before?

5. What’s the most embarrassing thing that’s ever happened to you?

6. Have you ever had a one-night stand?

7. What’s the most daring thing you’ve ever done?

8. Have you ever had a threesome?

9. What’s the most reckless thing you’ve ever done?

10. Have you ever lied to a partner and regretted it?

11. What’s the biggest risk you’ve ever taken?

12. Have you ever had a secret relationship?

13. What’s the most scandalous thing you’ve ever been involved in?

14. Have you ever been attracted to someone who’s off-limits?

15. What’s the most intense argument you’ve ever had with a partner?

16. Have you ever had a crush on someone while you were in a relationship?

17. What’s the most adventurous thing you’ve ever done sexually?

18. Have you ever had a one-night stand that turned into something more?

19. What’s the most rebellious thing you’ve ever done?

20. Have you ever done something that you’re ashamed of?

Also read: 50 Juicy questions to ask your boyfriend (over text or in person)

flirty questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Flirty questions to ask your boyfriend over text

These are some flirty questions to ask your boyfriend over text:

1. Would you like to come over so I can show you how much I miss you?

2. If I said I wanted to kiss you right now, would you let me?

3. What would you do if I showed up to your door in nothing but lingerie?

4. What’s the sexiest thing I could do for you right now?

5. What turns you on the most?

6. What’s the naughtiest thing you’ve ever thought of doing with me?

7. Could you do me a favor and take off all your clothes?

8. Are you thinking about me as much as I’m thinking about you?

9. Do you want me to whisper something naughty in your ear?

10. How would you feel if I started running my hands all over your body?

11. Do you wish you could be with me right now?

12. What would you do if I asked you to come over right now?

13. What would you do if I asked you to come over and wear nothing but your underwear?

14. If I asked you to do something naughty with me, would you do it?

15. What would you do if I asked you to kiss me right now?

16. Is there something special you would like me to do for you tonight?

17. Are you ready for me to show you how much I desire you?

18. If I told you I wanted you right now, would you come over?

19. Do you think you could handle me if I was to be a bit more adventurous?

20. Have you ever thought of something naughty you’d like to do with me?

intimate questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Cute, Romantic and Intimate questions to ask your boyfriend over text

Here is a list of cute, romantic and intimate questions to ask your boyfriend over text:

1. What’s your favorite part of my body?

2. What’s the hottest thing a girl has ever done for you?

3. What’s the sexiest outfit you’ve ever seen me wear?

4. Have you ever had a naughty dream about me?

5. If we were alone together right now, what would you do to me?

6. What’s the most sensual experience you’ve ever had?

7. What’s the most seductive thing a girl can do?

8. Have you ever fantasized about me while we were apart?

9. What’s the most erotic thing someone has ever said to you?

10. What’s the kinkiest thing you’ve ever done?

11. What’s your favorite thing to do in bed?

12. Have you ever thought about trying something new in the bedroom?

13. If we were in a crowded room, how would you show me that you wanted me?

14. What’s the most passionate kiss you’ve ever had?

15. What’s the sexiest quality someone can have?

16. What’s the most intimate experience you’ve ever had?

17. Have you ever had a spontaneous hookup?

18. What’s the wildest thing you’ve ever done with a partner?

19. What’s the sexiest thing you’ve ever said to someone?

20. If we could be intimate anywhere in the world, where would you choose?

awkward questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Awkward questions to ask your boyfriend over text

Here is a list of awkward questions to ask your boyfriend over text:

1. Have you ever had a crush on someone while we were together?

2. Have you ever had a dream about me that made you uncomfortable?

3. Have you ever accidentally called me by someone else’s name?

4. What’s the most embarrassing thing that’s ever happened to you during sex?

5. Have you ever lied to me about something important?

6. Have you ever farted in front of me and tried to pretend it wasn’t you?

7. Have you ever stolen something and not told anyone?

8. Have you ever been caught doing something you shouldn’t have been doing?

9. Do you have any secret fetishes or kinks that you haven’t told me about?

10. Have you ever cheated on a partner before?

11. Have you ever had a one-night stand?

12. What’s the weirdest thing you’ve ever eaten?

13. Have you ever had a wardrobe malfunction in public?

14. Do you still have feelings for any of your exes?

15. Have you ever been attracted to one of my family members or friends?

16. Have you ever secretly read my diary or gone through my phone?

17. What’s the most embarrassing thing you’ve ever done in front of me?

18. Have you ever peed in a pool or ocean when you weren’t supposed to?

19. Have you ever had a crush on someone of the same sex?

20. What’s the most embarrassing nickname you’ve ever had?

dirty questions to ask your boyfriend over text 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

Dirty questions to ask your boyfriend over text

These are a few more dirty questions to ask your boyfriend over text:

1. What are you wearing right now?

2. What kind of naughty things can I do to you tonight?

3. Is there anything you would like me to do to you that you’ve never asked for before?

4. Would you let me tie you up and have my way with you?

5. What would you do if I showed up at your door right now wearing nothing but a smile?

6. What’s the naughtiest thing you’ve ever done?

7. Do you like it when I talk dirty to you?

8. What’s the most daring sexual experience you’ve ever had?

9. Would you let me blindfold you and do whatever I want?

10. What’s the wildest fantasy you’ve ever had?

11. What turns you on more, kissing or touching?

12. Would you let me spank you?

13. What do you like most about my body?

14. Do you like it when I’m rough or gentle during sex?

15. What do you think would be the hottest thing to do together right now?

16. What do you think about when you think about me?

17. How would you feel if I kissed you all over your body?

18. What do you think would be the hottest thing to do together right now?

19. If you could do anything to me in bed right now, what would it be?

20. Do you like it slow and gentle or hard and fast?

Also read: 100+ Sexual questions to ask your boyfriend (very sexy, intimate, flirty, romantic and fantasies about sex)

Good and Interesting questions to ask your boyfriend over text at night

Here are a list of good and interesting questions to ask your boyfriend over text at night:

1. What’s one thing you’re grateful for today?

2. If you could travel anywhere in the world, where would you go and why?

3. What’s one thing you’ve always wanted to learn, but haven’t had the chance to yet?

4. What’s the last book you read, and what did you think of it?

5. If you had to describe your ideal day, what would it look like?

6. What’s one thing that always makes you feel better when you’re feeling down?

7. If you could have dinner with any historical figure, who would it be and why?

8. What’s one thing you’re looking forward to in the near future?

9. What’s one thing you’ve accomplished recently that you’re proud of?

10. If you could switch lives with someone for a day, who would it be and why?

11. What’s one thing you wish you could change about the world?

12. What’s the most meaningful gift you’ve ever received?

13. If you could only eat one type of cuisine for the rest of your life, what would it be?

14. What’s your favorite way to spend a lazy day?

15. What’s one thing you’ve always wanted to do, but have been too scared to try?

16. If you could have any superpower, what would it be and why?

17. What’s the most interesting thing you’ve learned recently?

18. What’s your favorite childhood memory?

19. What’s one thing you want to accomplish in the next year?

20. If you could go back in time and relive one moment from your life, what would it be?

Serious questions to ask your boyfriend over text

These are some serious questions to ask your boyfriend over text:

1. What are your long-term goals in life?

2. What are your biggest fears, and how do you deal with them?

3. What do you think are your biggest strengths and weaknesses?

4. What do you value most in a relationship?

5. How do you handle conflicts or disagreements in a relationship?

6. What’s the biggest challenge you’ve faced in your life so far, and how did you overcome it?

7. What motivates you to keep going when things get tough?

8. How do you prioritize your time and energy in your daily life?

9. What kind of legacy do you want to leave behind?

10. What are your thoughts on marriage and family?

11. What kind of impact do you want to have on the world?

12. How do you define success in your life?

13. What kind of personal growth have you experienced in the past year?

14. How do you handle stress and pressure?

15. What are your thoughts on mental health and self-care?

16. How do you balance your personal life with your career or other responsibilities?

17. What kind of role do you see communication playing in a healthy relationship?

18. What are your thoughts on religion or spirituality?

19. How do you define happiness?

20. What do you think is the most important quality in a partner?

Truth or dare questions to ask your boyfriend over text

Here is a list of truth or dare questions to ask your boyfriend over text:

Truth:

1. Have you ever lied to me about something important? If so, what was it?

2. Have you ever stolen anything before? What was it?

3. Have you ever been attracted to one of my friends? Who?

4. Have you ever cheated on a test or exam?

5. Have you ever pretended to like something just to impress me?

6. Have you ever had a crush on a teacher? Who?

7. Have you ever lied to get out of trouble? What did you say?

8. Have you ever faked being sick to get out of work or school?

9. What’s the biggest secret you’ve ever kept from me?

10. Have you ever done something illegal? What was it?

Dare:

1. Take a selfie wearing nothing but your underwear and send it to me.

2. Do 10 push-ups in a public place and post a video of it on social media.

3. Call your best friend and tell them you’re breaking up with them (as a joke).

4. Sing a song in a public place and post a video of it on social media.

5. Take a shot of hot sauce or eat a spoonful of wasabi.

6. Send a funny meme to your boss or coworker.

7. Do a silly dance in a public place and post a video of it on social media.

8. Call your mom and ask her to pick you up because you got lost.

9. Go up to a stranger and ask them for a piggyback ride.

10. Text your crush and tell them how much you like them (as a joke).

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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