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

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Get to know him better with these sweet and spicy questions
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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

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  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?
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Section 2 of 5:

Romantic Questions

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  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:”
    • 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?
Section 3 of 5:

Spicy Questions

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  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 . [3] 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?
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Section 4 of 5:

Funny Questions

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  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.” 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: [4]
    • 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

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  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 : [5]
    • 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?
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      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.”
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      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. ↑ https://www.health.harvard.edu/mens-health/get-back-in-sexual-sync
      4. ↑ https://www.betterhelp.com/advice/relations/how-well-do-you-know-me-questions-25-questions-for-couples/
      5. ↑ https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner#questions

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