105 Flirty, Cute, & Deep Questions to Ask Your Boyfriend

PDF download Download Article
Get to know him better with these sweet and spicy questions
PDF download Download Article

Looking for ways to learn more about your boyfriend and make him feel desired? Asking fun and juicy questions is one of the best ways to bond as a couple, even if you’re not in the same room. We interviewed professional dating experts to create the ultimate list of flirty questions to ask your boyfriend. From romantic and spicy to silly and deep, here’s everything you need to crank up the heat and build intimacy in your relationship.

Section 1 of 5:

Flirty Questions

PDF download Download Article
  1. Looking for ways to spice things up and make your boyfriend feel desired ? Find out his fantasies and turn-ons to keep him on his toes! Asking these flirty questions can increase intimacy and attraction with your partner, plus bring passion back into your relationship : [1]
    • What’s your usual type?
    • What’s your biggest turn on?
    • Who’s your celebrity hall pass?
    • What song puts you in the mood?
    • Do you prefer kissing or cuddling?
    • What was your sexual awakening?
    • Would you ever visit a nude beach?
    • What’s your biggest guilty pleasure?
    • Have you ever gone skinny dipping?
    • What was your first impression of me?
    • What’s your favorite body part of mine?
    • Have you ever been turned on at work?
    • What’s your favorite place to be kissed?
    • What outfit do you think I look the sexiest in?
    • What’s your hottest memory of the two of us?
    • What’s the best pick-up line you’ve ever used?
    • If you could be me for a day, what would you do?
    • What’s the first thing you told your friends about me?
    • If you could describe me in one word, what would it be?
    • Did you stalk me on social media before we started dating?
    • What do you think your 13-year old self would think about who you ended up with?
    • Need more flirtatious ideas? Join the conversation at our "What are some flirty questions to ask a guy?" forum !
    2. Advertisement
Section 2 of 5:

Romantic Questions

PDF download Download Article
  1. If you want to connect with him on a deeper level , open up and show off your soft side. Ask your boyfriend about his relationship expectations and overall outlook on love to determine if you’re compatible, or take a love language quiz and discuss your results. [2] According to matchmaker Erika Caplan, it’s important to “communicate what you need in a relationship” since “people receive and give love in different ways:” [3]
    • What’s your love language?
    • Do you believe in soulmates?
    • What does love mean to you?
    • Do you believe in twin flames?
    • What song makes you think of me?
    • Do you believe in love at first sight?
    • What’s your idea of the perfect date?
    • How did you know that I was into you?
    • When’s the last time you felt butterflies?
    • What’s something that reminds you of me?
    • What do you find most attractive about me?
    • What’s the first thing you noticed about me?
    • When did you realize you had feelings for me?
    • What’s something new you’d like to try together?
    • If we had a Netflix show, what would it be called?
    • What’s your favorite thing about our relationship?
    • What’s something I can do to strengthen our relationship?
    • If we had to move to another country, where would we live?
    • How would you approach me if we weren’t in a relationship?
    • If you could relive one day in our relationship, what would it be?
    • Reader Poll: We asked 131 wikiHow readers how they like to show love to their partner, and 50% of them said through physical affection, like hugs and kisses. [Take Poll] Learning your partner’s love language is a great way to determine how to show your love.
Section 3 of 5:

Spicy Questions

PDF download Download Article
  1. Trying to get your boyfriend all hot and bothered? Shift your questions from flirty to dirty! By discovering his sexual preferences and desires, you can improve your sex life and become irresistible in the bedroom . [4] Ask your boyfriend the following questions to turn him on and build sexual tension :
    • Giving or receiving?
    • Do you like dirty talk?
    • Do you have any fetishes?
    • What’s your biggest fantasy?
    • What’s your favorite position?
    • What’s your wildest sex story?
    • How do you feel about role play?
    • Have you ever made a sex tape?
    • What’s your go-to porn category?
    • Fast and fiery, or slow and sensual?
    • How often do you want to have sex?
    • Have you ever fantasized about me?
    • What’s your favorite part of foreplay?
    • Have you ever been caught in action?
    • Have you ever been caught in action?
    • Do you prefer being on top or bottom?
    • Do you prefer a screamer or a moaner?
    • Do you prefer morning sex or night sex?
    • Where’s the weirdest place you’ve had sex?
    • What’s the longest you’ve gone without having sex?
    • What’s one thing you would change about our sex life?
    • What’s your most awkward or embarrassing sexual encounter?
    2. Advertisement
Section 4 of 5:

Funny Questions

PDF download Download Article
  1. Throw in silly questions to make your boyfriend laugh out loud. According to dating coach and matchmaker Laura Bilotta, “the goal of joking around with a guy is to build a connection and create a fun, lighthearted atmosphere.” [5] If your boyfriend is having a bad day, ask goofy questions to lighten the mood. Come up with weird and wacky “would you rather” style questions or ask him about his most embarrassing or awkward encounters: [6]
    • What gives you the ick?
    • What’s your most useless skill?
    • What’s your biggest irrational fear?
    • Do you think a hot dog is a sandwich?
    • What’s the worst text you’ve accidentally sent?
    • Would you rather be bald or have no eyebrows?
    • What’s the best prank you’ve pulled on someone?
    • Would you rather always shout or always whisper?
    • What’s the most embarrassing thing in your closet?
    • What’s the dumbest thing you’ve done while drunk?
    • What’s the funniest thing you believed in as a child?
    • If animals could talk, which one would be the rudest?
    • If you could fight any historical figure, who would it be?
    • Would you rather wear orange Crocs or Big Red Boots?
    • What’s the most unnecessary white lie you’ve ever told?
    • What’s an embarrassing song or band you secretly love?
    • What’s one inanimate object you would delete from existence?
    • What’s the most savage insult you can come up with on the spot?
    • What’s the weirdest or most shocking thing you’ve seen in someone’s house?
    • Would you rather always feel like you have to sneeze or sneeze 500 times a day?
    • Would you rather talk like Mickey Mouse when you’re angry or turn into the Hulk when you’re turned on?
Section 5 of 5:

Personal Questions

PDF download Download Article
  1. If you want to deepen your relationship, ask your boyfriend meaningful questions that move beyond the surface. Talk about his dreams, goals, and childhood memories—then, prepare to do the same! Asking deep and personal questions is the best way to increase trust and feel close to your partner : [7]
    • Who’s your hero?
    • What brings you joy?
    • When did you last cry?
    • What’s your greatest fear?
    • What’s your top goal in life?
    • What’s your biggest insecurity?
    • What are you most grateful for?
    • What are you the most proud of?
    • What’s your biggest regret in life?
    • What’s your definition of success?
    • What’s your favorite way to unwind?
    • What’s something on your bucket list?
    • Do you care what people think of you?
    • Where do you see yourself in 10 years?
    • What’s your favorite childhood memory?
    • What are 3 things you love about yourself?
    • How have you changed in the past 5 years?
    • What’s something you’ve never told anyone?
    • Do you think physical or emotional pain is worse?
    • What did you want to be when you were younger?
    • What’s the best piece of advice you’ve ever received?
    2. Advertisement

Join the Discussion...

What are questions guys love to be asked?
wikiHow Editorial Team
Looking for some great questions and conversation starters to try out on your crush? We’ve got you covered! Here are some questions that guys love to be asked (and guys, feel free to add your personal favorites in the comments below!):
  • What movie or TV show can you watch over and over again?
  • What’s something that most people wouldn’t guess about you?
  • What achievement are you most proud of?
  • Do you have a favorite quote or motto that you find inspiring?
  • What’s the most important lesson you’ve ever learned?
  • What would the perfect date look like to you?
  • What’s your favorite way to express love or appreciation for someone?
Read Discussion

Expert Q&A

Ask a Question
200 characters left
Include your email address to get a message when this question is answered.
Submit
      Advertisement

      Tips

      • If you’re dating a shy guy, he might feel uncomfortable or overwhelmed opening up to you. Start off with fun and flirty questions, then ask him if it’s okay to bring up more serious topics. Dating coach John Keegan advises to “go slow” and “give him space to enter the conversation.” [8]
        Thanks
        Helpful 2 Not Helpful 2
      Submit a Tip
      All tip submissions are carefully reviewed before being published
      Name
      Please provide your name and last initial
      Submit
      Thanks for submitting a tip for review!
      Advertisement

      You Might Also Like

      170+ Deep, Heartfelt & Passionate Love Messages to Send Your Guy
      How to
      Make Your Girlfriend Want to Have Sex With You
      How to
      Prepare for Your First Time for Guys
      How to
      Turn a Girl On
      45 Sweet Paragraphs That’ll Make Your Girlfriend Cry
      150+ Romantic & Funny Questions to Make Your Boyfriend Laugh
      28 Funny Jokes to Tell Your Girlfriend
      How to
      Tell if Your Boyfriend Is Gay
      How to
      Kiss Your Boyfriend to Make Him Crazy
      How to
      Turn On Your Girlfriend
      How to
      Get Your Boyfriend's Attention Sexually
      50+ Conversation, Board, and Video Games to Play with Your Girlfriend
      How to
      Create Sexual Tension
      Romantic and Thoughtful Texts to Send to Your Boyfriend to Make Him Feel Special
      Advertisement

      References

      1. ↑ https://www.betterhelp.com/advice/relations/how-well-do-you-know-me-questions-25-questions-for-couples/
      2. ↑ https://www.helpguide.org/articles/relationships-communication/tips-for-finding-lasting-love.htm
      3. ↑ Erika Kaplan. Relationship Advisor. Expert Interview
      4. ↑ https://www.health.harvard.edu/mens-health/get-back-in-sexual-sync
      5. ↑ Laura Bilotta. Dating Coach & Matchmaker. Expert Interview
      6. ↑ https://www.betterhelp.com/advice/relations/how-well-do-you-know-me-questions-25-questions-for-couples/
      7. ↑ https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner#questions
      8. ↑ John Keegan. Dating Coach. Expert Interview

      About This Article

      In other languages
      Thanks to all authors for creating a page that has been read 76,592 times.

      Did this article help you?

      Advertisement