From Crushes to Sex: 125 Juicy Questions You’re Dying to Ask Your Boyfriend

Want to find out all your boyfriend's juicy secrets and deepest desires? 

Asking the right questions can take your relationship to the next level by building intimacy and trust. 

We've got 100 cheeky, flirty, and revealing questions guaranteed to spice up your love life and get the conversation flowing

From probing about his past relationships and conquests to finding out his kinkiest fantasies, this list has everything you need to discover new sides of your man and get closer than ever before. 

So set aside some private time, have an open mind, and get ready to learn some saucy new details!

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100 Juicy Questions to Ask Your Boyfriend

Now that you're ready to heat things up, it's time for the main event – 100 juicy, thought-provoking questions that will get your boyfriend chatting about intimate topics ranging from past loves to sexual desires. 

couple laying on bed talking Juicy Questions to Ask Your Boyfriend

Use these to spark deep conversation and learn more about the guy you care so much about.

1. What's your biggest relationship regret?

We all have things we wish we had done differently in past relationships. This introspective question allows him to open up about his dating history and what he's learned from it while showing you care about who he is today. 

2. When did you first fall in love?

Learning about his first major crush or early romantic experience provides insight into how your boyfriend views love and relationships. Pay attention to how he describes the emotions and attachments.

3. What's one thing you'd change about me? 

While a risky question, asking this shows you're open to constructive criticism and want to improve yourself for him. Make sure to have a sincere, non-defensive reaction to build trust.

4. What's your love language?

Does he prefer acts of service, physical touch, or words of affirmation? Knowing how he feels most loved can help you express affection in ways he best understands.

5. How do you handle disagreements in relationships?

Fighting is inevitable – uncovering his usual conflict style gives you clues to prevent future arguments and diffuse tense situations thoughtfully when they arise.

6. What do you find sexiest about me?

An ego boost for you both! His answer allows you to know what attracts him most so you can highlight those parts of yourself. It also gets him thinking sexy thoughts.

7. What's your biggest fear in our relationship? 

Vulnerability is intimacy – this question reveals his inner worries and can prompt reassurance from you to alleviate them.

8. What's your biggest fantasy?

Maybe you can make it come true! This juicy question lets you know exactly what turns him on most and how you can get creative in the bedroom.

9. Where's the most public place you've had sex? 

Fun and a little naughty, this invites him to share wild past exploits and perhaps set the stage for some risky adventures of your own.

10. What's something I do that turns you on every time?

Give your ego a little rub and find out what never fails to get him hot and bothered when you do it. Then you can amp it up and drive him wild.

11. What's the fastest you've gone from meeting someone to sleeping with them? 

This reveals his views on casual sex and potentially his adventurous side. Pay attention to whether he shares any regret or seems proud of his experience. 

12. When was your first time, and how was it?

His first sexual experience says a lot about how he views intimacy and relationships. Listen for emotional maturity and if he respects his past partners.

13. Have you ever cheated on a partner? Why or why not?

Infidelity can be a touchy subject, so tread carefully. But, understanding his beliefs around loyalty can prevent heartbreak.

14. What's the longest you've gone without sex while in a relationship? 

Periods of celibacy can strain couples – this question provides insight into his libido and how you can both stay satisfied.

15. What makes you feel emotionally close to someone?

Whether it's cuddling, deep talks, or acts of service, knowing his emotional love language is key to keeping your bond tight.

16. What are you most self-conscious about in bed?

If he opens up with insecurities, you can gently reassure him and make intimacy more enjoyable for you both.

17. What's one sexual act you won't do and one you love?

Understanding his hard and soft limits prevents pushing unwanted boundaries in the heat of the moment.

18. When do you feel the sexiest?

Discover what situations make him ooze confidence so you can stoke the fire and enjoy the results together.

19. What item of clothing do you love seeing me in?

Catering to his preferences boosts your confidence and his arousal when you dress to impress.

20. What's your favorite romantic song?

Music is powerful – finding out his romantic anthem provides insight into how he views love and creates a chance for you to serenade him.

21. Where's your most sensitive spot?

Use this intel to lavish extra attention on the areas that drive him wild when touched the right way. 

22. What's the steamiest dream you've had about me? 

Flattering and scintillating! This question lets you know what fantasies he harbors about you between the sheets.

23. What's your favorite body part of mine? 

Hearing which part he admires most will give you a confidence boost, so accentuate it by highlighting that area when you dress up for a special date night together.

24. What's the most adventurous place you'd be down to have sex? 

Finding out where he'd like to get frisky outside the bedroom provides insight into his comfort with public play and creates an opportunity to explore new thrills as a couple.

couple sitting on sofa smiling Juicy Questions to Ask Your Boyfriend

25. Slow and gentle or rough and passionate – which do you prefer? 

Everyone has different preferences in pace and intensity when making love, so this question helps you learn his tastes intimately; keep the conversation going by sharing your own inclinations as well.   

26. What's the hottest photo you've ever taken for a partner? 

His response may surprise you with saucy details about past sexual exploits while inviting flirty reminiscing if you ask for a private repeat performance.

27. Have you ever gotten frisky in public? 

Tell me about it. PDA preferences fall along a spectrum, so this question reveals what his comfort level is for amorous adventures beyond the bedroom and if exhibitionism intrigues him. 

28. What's your hottest unfulfilled desire? 

Fantasies can be deeply personal, but sharing them builds intimacy; listen with an open mind, then reciprocate by revealing your own wildest dream and seeing where the conversation leads you both.

29. When did you first realize you were falling for me? 

It's endearing to reminisce about early relationship milestones, so this sweet question invites him to open up about when his feelings deepened, shedding light on your romantic beginnings.

30. If you could change one thing about your sex life with me, what would it be? 

While a risky question, it shows your openness to constructive criticism and desire to improve your intimate connection, so listen earnestly without getting defensive.

31. What's something naughty you've secretly wanted to try in public? 

Some adventurous couples crave thrills through public sexual play. This invites him to share a fantasy you may want to explore together, but set clear boundaries first and never exceed your comfort levels.

32. What's something you're dying to try in bed but have been too shy to bring up?

We all have unspoken desires. This gives him the green light to share intimate fantasies he's been afraid to voice. Keep an open mind and see if you're willing to experiment together.

33. When do you feel most connected emotionally and physically? 

Understanding the situations that make him feel closest to you, body and soul, can help maximize tender moments. Share when you feel most bonded as well.

34. What's one sexual act that you dislike and never want me to do?

It's important to respect each other's hard limits. This question allows him to explain any acts that are off the table so you never cross those boundaries unintentionally.

35. Of all your past partners, who did you have the best physical chemistry with?

While a bit risky, this provokes him to reflect on past passionate connections. Focus less on comparisons and more on what stood out so you can learn new techniques.

36. What's something you'd love me to wear for a night of passion?

Catering to his fantasy wardrobe provides titillating anticipation. Bonus points if you surprise him by dressing up when he least expects it. 

37. Have you ever faked an orgasm with me? When and why?

If he says yes, this can guide an open conversation about your mutual pleasure and satisfaction. You can brainstorm new ways to enhance intimacy.

38. Where would you love to have sex that we haven't yet?  

This cheekily invites him to divulge adventurous fantasies you haven't explored yet. Discuss whether you're both game to make it a reality.

39. When do you feel most emotionally vulnerable during sex?

Understanding when he feels extra sensitive can help you provide reassurance and validate his emotions in those moments.

40. What's your biggest turn-off in bed?

Knowing these allows you to avoid mood-breaking mistakes. Share yours as well, so you're both aware of total mood-killers.

41. What's one thing you wish I'd be more open-minded to try sexually?

Maybe he fantasizes about something you've rejected before. This gives you a chance to reconsider hard limits and try expanding your comfort zone.

42. What's the most spontaneous or daring thing you've done in a relationship? 

Revealing his boldest romantic gestures and adventures shows how he pursues excitement and if you share similar passion levels. Reciprocity by sharing your own exploits can lead to future thrills.

43. Which of my friends do you find most attractive? 

While a bold question, his answer spotlights his taste and type beyond just you. Keep it lighthearted and focus on his reasons rather than comparisons. 

44. What's your love life fantasy that we haven't made a reality yet? 

Fantasies reveal desires, allowing him to get provocative about unfulfilled dreams you could explore together. Ensure mutual comfort levels before planning anything. 

45. Have you ever been attracted to a friend's significant other? Why? 

Crushes happen, so his honesty shows maturity if handled appropriately in the past. Discuss healthy boundaries around platonic friendships going forward.

46. Where on my body do you wish I had more hair and less hair? 

We all have grooming preferences, but voicing them feels awkward. This playful question opens the conversation so you can align styles or stick with your own.   

47. Do you have any turn-ons I'm unaware of? 

Think you know them all? Let this draw out the juicy details he may not have vocalized yet. Say whether you're willing to indulge them.

48. Which of your exes were best in bed – what did they do well? 

While risky territory, this can unearth techniques to wow him by learning from past lovers' talents. Keep jealousy at bay and focus on the wisdom gained.

49. Have you ever been to a strip club? What did you love and hate about it? 

His reaction reveals views on monogamy and women's sexuality. Listen for maturity, then ask if he'd be okay with you attending a male revue. 

50. How do you most enjoy receiving sensual pleasure without actual sex? 

Getting frisky doesn't require going all the way. Find out his favorite activities so there are no limitations on intimacy. 

51. In what public place would secretly turn you on to get it on? 

Sexual exhibitionism has appeal for some. This probing question tests the waters for adventurous – albeit risky – new avenues of expression.

woman laying on mans lap on sofa Juicy Questions to Ask Your Boyfriend

52. What's the most surprising place you've had sex, and how was it? 

Past wild exploits build intimacy if you're both comfortable being candid. Let his story lead to sharing your own as you relive the thrill.

53. Have you ever faked being sick to get out of sex? Why? 

Difficult conversations strengthen bonds. If he says yes, use empathy and uncover how to avoid those situations again.

54. What celebrity do you have a secret crush on? 

We all have fantasies beyond our partners. This probes who stimulates him mentally and physically when you're apart. 

55. What public places have you thought about getting frisky in? 

Fantasies abound. This reveals his secret turn-ons for public play and aligns your comfort levels to avoid going too far.

56. How do you prefer being touched during intimacy? 

Light scratching? Gentle kneading? Let him describe ideal pressure, speed, and motion so your touch fulfills him.

57. What song or movie always gets you in the mood? 

Using sensual cues that you know inspire him makes intimacy feel more natural when you need that spark.

58. Have you ever thought about someone else during sex with me? 

Be honest! We all have wandering minds. Handled with maturity, this builds understanding and forgiveness. 

59. What was your first impression of me physically and emotionally? 

It's endearing to reminisce over early interactions and attractions. Remembering your beginnings fosters appreciation.   

60. If you could have a threesome, who would you choose as the third person? 

This fantasy reveals desires he may not feel comfortable sharing yet. Keep jealousy aside as you discuss boundaries honestly.

61. What outfit do you think I look sexiest in? 

Catering to his preferences boosts confidence when dressing up, while his tastes provide insight to attract him visually. Share your thoughts on his most appealing looks as well.

62. Have you ever been walked in on having sex? When and what happened? 

This cheeky question uncovers adventures and mishaps that build intimacy through vulnerability. Discuss how to avoid awkward interruptions going forward.

63. What's something you wish I'd do more of in the bedroom? 

Everyone has unspoken desires – this opens the conversation so any bedroom improvements are voiced constructively. Offer your own wishes as well. 

64. What do you most hope our future sex life looks like? 

Visualizing your sexual aspirations together provides insight into aligning your passions as your relationship progresses through the years.

65. Is there any type of porn or erotic material that makes you uncomfortable? 

Boundaries surrounding pornography differ for everyone. This allows you to explain amicably what you both find acceptable or offensive.

Related: Is Watching Porn Cheating?

66. Have you ever sent a sext or nude photos? What was your experience? 

Sexting comfort levels vary, so find out if he's into it or if flirty messages suffice without pushing limits.

67. What has been your most memorable sensual experience so far in your life? 

Reliving exciting exploits builds intimacy. If it's something you shared, reminisce fondly. Otherwise, note what made it monumental.  

68. Have you ever hooked up with a coworker or acquaintance you shouldn't have? 

Office romances happen – see if his reflections show maturity in handling tricky connections. Share any relevant experiences of your own. 

69. What childhood misconceptions did you have about sex or relationships? 

Our naivety in youth can be hilarious in hindsight. Bond through laughter over mistaking myths for facts back in the day.

70. Do you have any kinks or fetishes I don't know about yet? 

There may be secret turn-ons he's hesitant to unveil. Express openness to discuss them without judgment when he's comfortable.

71. What's your hottest go-to fantasy when self-pleasuring? 

Masturbation provides insights into private desires. If he opens up, this mutual vulnerability can enhance intimacy and trust.

72. Have you ever faked not feeling good to avoid sex with me? Why? 

Faking excuses can damage trust and self-esteem if recurrent. Discuss honestly so you both feel satisfied with your intimacy. 

73. What song do you think captures the essence of our relationship? 

Music conveys emotion – this reveals how he views your bond. Share the song that sums up your love as well.

74. What's the most public place you'd be willing to get caught fooling around at? 

For some, extra thrills come from potential public exposure. This probes his willingness to get risqué.   

75. When do you feel our age difference most in our relationship? 

Being open about generational gaps prevents misunderstandings. Discuss how to embrace your differences positively.

76. Which friends of yours do I get along with, best and worst? Why? 

Honesty reveals his perspective on your friend dynamics. This cultivates self-awareness to build those relationships positively.  

77. Do you ever compare our sex life to past partners? Why? 

Bedroom comparisons breed insecurity, but they do happen. If he says yes, reaffirm your commitment to mutual satisfaction. 

78. What could I do to be a more supportive partner? 

Self-improvement insights show your dedication. Listen intently, then share what support means most to you.

79. Do you have any secret hobbies I don't know about yet? 

We need independent fulfillment, too. Nurture trust by sharing his hidden interests without judgment, and he'll likely reciprocate.

80. Have you ever questioned my loyalty or faithfulness? Why? 

Jealousy damages relationships but is natural. This vulnerability strengthens bonds if you both want to resolve lingering doubts.

81. Which of my personality traits did you notice first? 

Early impressions reveal initial attractions. Asking shows interest in how his feelings developed while sharing yours fosters reminiscence. 

82. What bad habits do I have that bother you? 

Improving ourselves for our partners deepens bonds. Listen sincerely, then lovingly explain your pet peeves of his so you're both aware.

83. How do you best feel emotionally valued in a relationship? 

Everyone expresses and receives love differently. Understanding his emotional needs prevents future disconnects and resentment.  

84. Which positions do you enjoy most and least? 

Sex provides peak intimacy when fully mutually enjoyable. Guiding each other to favorite pleasurable positions will bring you closer and make intimacy more fun. 

85. What romantic gesture have you always wanted to experience? 

Making his relationship dreams a reality conveys devotion if they resonate with you. Share yours for future inspiration, too.

86. What's something I could change about my kissing style? 

There's always room for growth in intimacy. Welcoming constructive feedback without offense strengthens connections.

87. Have you ever gotten back with an ex? Why did you break up initially? 

Understanding past relationship patterns provides insight into potential future conflicts to avoid. 

88. Do you have any secret fears about fully committing to me? 

Cold feet is normal, but discussing doubts can lead to reassurance. Share yours so you're both secure.

89. What do you find most attractive and unattractive in people's personalities? 

Knowing his preferences highlights your compatible traits and growth areas to work through.

90. Which close friend do you think I get along with least? Why? 

Perceptive observations can increase self-awareness in relationships. Discuss mindfully and avoid defensiveness. 

91. Have you ever felt pressured to do more sexually than you wanted? 

Rebuilding trust requires openness if boundaries were crossed. Emphasize your respect for consent.

92. Do you have any anxieties about our future I can help soothe? 

Addressing worries jointly dispels negativity and reinforces your united front in overcoming obstacles. 

93. What bad habits have you picked up from me? 

Laughing over each other's quirks lightens the mood. Also, discuss more serious influences to improve yourselves.

94. What could I do more of in our relationship? 

Reflect sincerely on his requests and share yours to build habits that nurture your bond.

95. In what ways do we need to improve our sexual communication? 

Strong intimacy requires utter comfort in voicing desires and limitations. Brainstorm what builds that trust.

96. Have you ever felt insecure or jealous about any of my platonic friendships? 

Mutual understanding defuses suspicion between friends. This builds reassurance.

97. How could I make you feel more comfortable being emotionally open with me? 

Vulnerability strengthens connections but requires safety. Discuss how to provide that refuge. 

98. Are there any behaviors I exhibit that feel controlling or make you feel restricted? 

Care and control differ – shed light amicably on anything that feels stifling. 

99. What could I do to make you feel more loved every day? 

Small daily acts cultivate substantial bonds. Implementing his requests makes him feel cherished.

100. Why do you love me? 

Heartfelt reminders rekindle fondness. Explain all the reasons he's special to you as well.


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BONUS: 25 Freaky Questions to Ask Your Boyfriend

Ready to get naughty? Here are some extra spicy questions that take things to the next level. Be prepared for conversations that are totally taboo and reveal your deepest, darkest desires. Unlock adventurous new experiences as a couple by boldly exploring boundaries and fantasies in detail.

101. What's the naughtiest thing you've ever done in public?

Pushing comfort zones reveals adventurous sides; his answer may surprise you. Discuss how daring you're each willing to be sexually beyond privacy.

102. What sex act do you think is overrated?  

Understanding turn-offs prevent pressuring unwanted acts. Share yours, too, then redirect energy to mutually enjoyable bedroom activities.

103. Have you ever had a threesome? How was it?

If he says yes, this invites intimate details about his past exploits and perspectives on non-monogamy in a judgment-free zone.

104. Is there a kink you think I'd find weird?

We all have secret turn-ons that feel embarrassing. This gently coaxes his innermost desires without shaming, building trust and understanding.

105. Do you like being submissive or dominant in bed?

Power dynamics provide thrills for some. Discussing comfort levels helps you align preferences so intimacy is satisfying.

106. What kind of roleplay scenario have you secretly fantasized about trying? 

Roleplaying allows you to safely act out exciting personas and power dynamics. If he opens up, keep an open mind and discuss scenarios you'd like to explore together.

107. What's the sluttiest outfit you'd love to see me wear?

Catering to fantasies provides excitement. Bonus if you model it for roleplaying when the mood strikes.

108. What's the most public place you'd be down to have sex?

Risky romps hold appeal for some couples. This reveals locations he fantasizes about that you may share an interest in, too. 

109. What fetishes pique your curiosity?

We all wonder about taboos. Sharing intriguing concepts expands your sexual horizons and deepens intimacy through vulnerability.

110. Have you ever hooked up with a stranger? Tell me about it.

One-night stands reveal comfort with casual connections. Listen without judgment, focusing on safety.   

111. What's the most unique place you've gotten frisky?  

Wild exploits build bonds when you're both comfortable being candid. Let his story lead to sharing your own.

112. What's your hottest secret fantasy involving me?

This unveils provocative desires he may feel shy vocalizing. Keep jealousy aside as you listen and reciprocate. 

Understanding turn-offs prevents pressuring unwanted acts as you keep your intimate life exciting together.

114. Have you ever filmed yourself having sex?

Sexting and recording can be alluring but risky. Discuss your comfort levels to avoid exceeding boundaries. 

Laughter relieves tension. Swapping mortifying but hilarious mishaps brings you closer through vulnerability.

116. Have you ever purchased or used sex toys?

Toys provide pleasure, but opinions vary. This opens the conversation to enhance your intimate connection.

117. What's your top sexual dealbreaker?

Respecting each other's hard limits is crucial. Clearly convey what's off the table so it's never breached. 

118. Have you ever gotten aroused at an inappropriate time?

We've all been there! Swapping anecdotes about awkward public excitement relieves tension with humor.

119. What's the most unusual object you've used for stimulation?

Improvising thrills with household items can be a stimulating topic. Discuss how open you are to experimental props.   

120. What risky public place do you fantasize about doing it at?

Exhibitionism has appeal for some. Brainstorm adventurous yet safe outlets for public passion.

121. What would your dream oral pleasure involve?

Oral pleasure provides intimacy. Describing ideal techniques ensures fulfillment. Reciprocate desires too.

122. Have you ever engaged in roleplaying or dressed up during sex?  

Fantasies feel exciting made real – ask about any he enjoys and share your own open-mindedly.

123. What sex positions do you fantasize about trying but haven't yet? 

Expanding your repertoire together ensures peak satisfaction. Align comfort levels before any experiments.

124. Have you ever had sex with someone much older/younger than you? 

Age gap experiences can be insightful, but handle the question sensitively. Keep any judgment aside.

125. Where is the most public place I could seduce you?

Sparking passion in daring locations provides a thrill if you're both comfortable. Discuss boundaries.

How to Use These Freaky and Juicy Questions to Ask Your Boyfriend

Now that you have an arsenal of tantalizing questions for your man, it's time to put them to good use! Follow these tips to integrate them into your relationship seamlessly:

  • Set the mood. Pick a relaxing time when you're both in a positive mindset. Dim the lights, light candles, pour some wine – create an intimate ambiance conducive to deep conversation.
  • Take turns. Don't bombard him with questions. Ask one, share your own thoughts, and then let him ask you one. Making it a two-way dialogue builds comfort.
  • Know when to stop. If you hit a sensitive subject and either of you feels uncomfortable, it's okay to switch topics. These conversations require mutual willingness.
  • Don't judge. Listen with empathy and an open mind, not criticism. Trust is vital for honest sharing. Offer reassurance if needed.
  • Apply what you learn. Once you uncover new turn-ons and desires, put them into play! Trying new things together is half the fun.
  • Circle back around. Revisit the questions periodically to learn and share more as intimacy deepens over time. The goal is to boost your lifelong connection.

With the right approach, these juicy and freaky questions will allow you to discover steamy new sides of your man in a judgment-free zone. Have fun bonding and getting closer!

Final Thoughts

At the end of the day, asking these provocative questions is about more than just collecting spicy details or fantasies from your boyfriend. It's about building trust, comfort, empathy, and true intimacy in your relationship by mutually sharing vulnerabilities, desires, and insights into who you are at the core. Keep communicating, listening, and learning together always.