Every relationship can benefit from a little fun and intimacy. Whether you’ve been together for years or are still in the early stages of your relationship, asking the right questions can strengthen your bond and spice things up. A playful, flirtatious, or even a little naughty conversation can break the ice, ignite new desires, and bring you closer. If you’re looking for a way to bring some excitement into your relationship, then asking your boyfriend these 101 extremely dirty questions is the perfect way to do so. These questions cover a wide range of topics, from lighthearted and fun to deep and sensual, ensuring that no matter your mood, there’s something here to spark an unforgettable conversation.

1. Playful Icebreakers
- What’s the most embarrassing thing you’ve ever done for me?
- How would you describe our first kiss in three words?
- If I were a superhero, what would my superpower be?
- What’s the funniest thing I’ve done that made you laugh out loud?
- If you could describe me in one word, what would it be?
- What’s the most mischievous thing you’ve ever done when we were alone?
- How would you feel if I surprised you with a romantic date night?
- Do you remember the first time you saw me and what you thought?
- What’s the most romantic thing you’ve done for someone?
- What’s something you would do to make me laugh instantly?
Related Article: 60 Truth or Dare Questions to Ask Your Crush and Build a Stronger Connection
2. Flirty Questions
- What would you do if we were alone for an entire weekend?
- What’s the naughtiest thought you’ve had about me recently?
- Do you like it when I take control, or do you prefer leading?
- What’s the most daring thing you’ve ever done in public?
- How do you feel when I tease you in front of others?
- Have you ever imagined us doing something naughty in public?
- What’s your favorite part of me to kiss?
- What turns you on the most about me?
- Do you prefer slow, sensual kisses or fast, passionate ones?
- What would you do if I kissed you in front of your friends?
3. Sexy and Steamy Questions
- What’s your favorite body part of mine?
- How do you like to be touched when you’re in the mood?
- What’s something I do that instantly turns you on?
- Would you want me to send you naughty texts during the day?
- Do you have a secret fantasy involving me?
- What would you think if I wore something really sexy just for you?
- What’s the most seductive thing I can do to turn you on?
- Do you like being kissed on your neck, or somewhere else?
- What’s the most romantic thing you can imagine doing with me?
- What do you think about when you’re really in the mood for me?
4. Deeply Sensual Questions
- How do you feel when I whisper something naughty in your ear?
- What’s the best way to keep you up all night?
- Would you want to try something new in bed?
- What would you do if I blindfolded you during our next time together?
- Do you prefer to be the one in control or the one who surrenders control?
- What’s your favorite kind of kiss from me?
- How would you react if I initiated something spontaneous in public?
- When you think of me, what do you picture in your mind?
- Do you prefer slow, sensual love, or fast, passionate love?
- Would you ever want to try role-playing with me?
5. Wild “What If” Questions
- What would you do if we were caught in the act?
- If we could have a 24-hour pass to do anything, anywhere, what would you do?
- If I asked you to take me somewhere private, no questions asked, where would it be?
- Would you rather make love in a secluded place or a more adventurous location?
- Would you want to try making out in public to see if we get caught?
- What’s the most outrageous thing you would do for me?
- What would you do if I kissed you unexpectedly in front of your friends?
- Would you ever let me take full control for an entire night?
- How would you feel if I sent you a sexy text right now?
- What would you do if I dared you to try something risky and naughty?
6. Kinky and Adventurous Questions
- Have you ever thought about trying bondage or something similar?
- Would you like to explore new positions in bed with me?
- Do you prefer the lights on or off when we’re intimate?
- Would you be interested in experimenting with toys in our relationship?
- How would you feel about trying something a little more adventurous like public play?
- What’s the wildest location you’d be willing to make love in?
- Would you want to tie me up or would you prefer I tied you up?
- Would you be willing to roleplay with me? If so, what character would you want to be?
- What’s something you’ve always wanted to try in the bedroom but haven’t yet?
- How would you feel about introducing a little kink into our relationship?
7. Deep Relationship Questions
- What’s one thing you love about our relationship that you don’t tell me enough?
- How do you feel when I give you compliments?
- What’s something about me that you find irresistible?
- How do you imagine our future together?
- What’s one thing you’ve always wanted to ask me but never did?
- When did you first know you were in love with me?
- What’s the most romantic date you’d want to have with me?
- How do you like to be shown affection when you’re feeling down?
- What’s the best way to make you feel wanted and loved?
- What do you think makes our relationship unique compared to others?
8. Fun “Would You Rather” Questions
- Would you rather kiss me in the rain or in front of a crowd?
- Would you rather go on a spontaneous road trip with me or a planned vacation?
- Would you rather spend a night in a hotel room together or under the stars?
- Would you rather surprise me with a romantic gesture or me surprise you?
- Would you rather always make love in the dark or with candles lit up?
- Would you rather go to a secluded beach or a quiet cabin in the woods with me?
- Would you rather have a romantic night in or a wild night out?
- Would you rather have a passionate night or a fun, lighthearted night together?
- Would you rather spend a whole day cuddling with me or being adventurous outside?
- Would you rather share your secrets with me or have me surprise you with mine?
9. Fun and Lighthearted Questions
- What’s the funniest thing you’ve ever done to impress someone?
- What’s your idea of the perfect lazy day with me?
- How would you feel about me giving you a massage tonight?
- What would you do if I kissed you in front of your friends?
- What’s one thing you’d never want me to do in public?
- What’s the most spontaneous thing you’ve done with me?
- What’s the first thing you think of when I’m not around?
- What’s the best prank you’ve ever pulled on me?
- What’s the most awkward moment you’ve had with me?
- How would you feel about us trying a fun activity we’ve never done before?
10. Exploring Fantasies
- What’s the craziest fantasy you’ve had about us together?
- Have you ever thought about a fantasy involving me that you haven’t told me yet?
- Would you want to act out one of your fantasies with me?
- How would you feel about me dressing up in a costume just for you?
- Would you like me to surprise you with a sexy lingerie set?
- What’s one fantasy you’ve always wanted to experience with me but haven’t yet?
- How would you feel if I took you somewhere private and set the mood for an intimate night?
- Would you ever want to try making a video together for fun?
- Would you want to go to a fancy restaurant dressed up, and then have a spontaneous night out afterward?
- Would you prefer us to explore our fantasies in private or share them with others?
11. Deep and Meaningful Questions
- What’s something you’ve always wanted to say to me but never did?
Conclusion:
Asking the right questions can make all the difference in your relationship, whether you’re looking to deepen your emotional bond or add some spice to your intimacy. These 101 extremely dirty questions will help both of you explore desires, share fantasies, and ultimately have more fun in your relationship. Whether you choose to ask a few playful questions or dive into deeper, more intimate topics, the key is to stay open-minded, communicative, and respectful of each other’s boundaries. Have fun with the process and enjoy every moment of the conversation!