The Best Questions to Ask Your Boyfriend or Crush

Learn something new about him with these deep and flirty questions

Whether you’re crushing hard or in a committed relationship, we've compiled all the best questions to ask the guy you're into. Take a look at these TikTok- and expert-approved options—from personal deep dives to flirty remarks, we have it all! So, scroll through our list, pick out a question, and toss it out there (in person or via text) to get a conversation started. We bet you’ll discover something new ( wink, wink ).
This article is based on an interview with our professional matchmaker and dating coach, Lauren Sanders, founder of Dating for the Soul. Check out the full interview here.

Section 1 of 6:

Deep Questions

  1. If you’re just starting to get to know him, try asking him something personal. These questions are a great way to discover his likes, dislikes, and passions. Basically, they’re an excellent way to learn if you’re truly compatible! Send him a round of these questions when you’re having a heart-to-heart or on the first or second date:
    • What’s your best quality?
    • What does love mean to you?
    • What’s your biggest accomplishment? [1]
    • How do you define success?
    • What can you not live without?
    • What’s your favorite holiday?
    • What do you want to be remembered for?
    • Where do you see yourself in 10 years?
    • What’s the best gift you’ve ever received?
    • What’s your biggest dream in life?
    • Are you spiritual or religious? [2]
    • What do you think the world’s biggest problem is?
    • What keeps you awake at night?
    • How do you deal with disappointment?
    • What would you do if you were a world leader for a day?
    • Tell me about your favorite place to travel. [3]
    • What do you care passionately about?
    • What are your guilty pleasures?
    • What was your childhood like?
    • Are you an introvert or an extrovert?
    • What’s your most embarrassing memory?
    • When was the last time you cried?
    • What’s on your bucket list?
    • What are you most proud of?
    • What’s your life mantra?
    • What was your first job?
    • What’s your biggest fear?
    • What’s your family like? [4]
    • What’s your favorite quote?
    • Did you have a childhood nickname?
    • What’s your happiest memory?
    • What’s one thing that can always make you smile?
    • Who inspires you most?
    • What’s your favorite place you’ve ever been to?
    • What’s your favorite song?
    • What’s your favorite book?
    • What’s your dream job?
    • Tell me about your dream home.
    • What’s your favorite animal?
    • What conspiracy theory do you believe in?
    • Do you collect anything?
    • What’s your favorite comfort meal?
    • What made you laugh today?
    • What are you thinking about right now?
    • What’s your favorite subject in school? [5]
    • What’s your favorite dessert?
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Section 2 of 6:

Flirty Questions

  1. Flirting isn’t always about body language and gentle touches—it’s also about what you say! Show him you’re interested or set the tone for a romantic evening by asking him a flirtatious question. These questions are perfect for a first date or if you’re hoping to put him in a romantic mood. Here are some questions to try:
    • What’s your favorite memory we’ve made together?
    • What’s your love language?
    • What’s your favorite pickup line?
    • Do you like making the first move?
    • Who’s your celebrity crush?
    • What was your most memorable first date?
    • What does your perfect date look like?
    • Who was your first crush?
    • When did you know you were into me?
    • How do you know when you really like someone?
    • Do you have a type?
    • What’s your ideal night in?
    • What puts you in a good mood?
    • Will you dance with me right now?
    • What was our first kiss like for you?
    • Do you believe in soul mates?
    • When are you going to ask me out?
    • What’s the most surprising thing about you?
    • Do you consider yourself romantic?
    • What do you think is the worst pickup line?
    • Do you prefer cuddling or kissing?
    • Tell me about the first time you fell in love. [6]
Section 3 of 6:

Fun Questions

  1. One of the best ways to capture a guy’s attention is to make him laugh! So, don’t hesitate to ask him the silliest question you can think of. Not only is this an excellent way to get to know him more, but it’s also a brilliant way to show off your humor and personality. Try some of these questions to start:
    • What’s the wildest thing you’ve ever done?
    • If you could have any pet in the world, what would it be?
    • What fictional character do you identify with most?
    • If you were a pizza, what would be your toppings?
    • If you were a flavor of ice cream, what would you be?
    • If you could go anywhere in the world, where would you go?
    • What’s your go-to karaoke song?
    • What food do you always crave?
    • Do you believe in aliens?
    • What’s your idea of a perfect snow day?
    • What’s the most overrated candy?
    • Would you ever want to be famous? [7]
    • What would you play if you could be good at any sport?
    • If you started a podcast, what would it be about?
    • What do you think the cutest animal is?
    • What TV show have you seen the most times?
    • What’s your most ridiculous pet peeve?
    • Will you teach me how to play the guitar?
    • Are you a morning person or a night owl?
    • Rain or snow?
    • What’s the strangest thing you’ve ever put on a sandwich?
    • Did you sleep with a stuffed animal when you were a kid?
    • Who’s your celebrity look alike?
    • What would you do if you won the lottery?
    • What meal can you cook best?
    • Do you think pineapple belongs on pizza?
    • What’s your go-to joke?
    • If you were a superhero, what would your power be?
    • What’s one thing you always have in the fridge?
    • Who would play you in a movie?
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Section 4 of 6:

Serious Questions

  1. Don’t be afraid to get serious with him and ask him about his wants and needs. Knowing what he’s looking for in a partner and understanding what he needs in a relationship can help you both in the long run. [8] So, think about tossing one or more of these questions his way to learn more about him:
    • What are you looking for in a partner?
    • Do you want kids? [9]
    • How’s your relationship with your family?
    • Do you get offended easily?
    • How would you describe your past relationships?
    • Where do you see this relationship going?
    • When you’re upset, what do you need most?
    • What’s something that offends you?
    • Do you have any regrets?
    • If you could change anything about yourself, what would you change?
    • Do you like PDA (public displays of affection)?
    • What are your relationship deal breakers?
    • Do you prefer spontaneous or planned dates?
    • What’s the best way I can support you?
    • How do you handle failure?
    • Do you want to get married one day? [10]
    • What’s the biggest mistake you’ve ever made?
    • Who do you think should pay for dates?
    • What do you think about public proposals?
    • How did you break up with your ex?
    • Have you ever broken the law or been arrested?
    • What cultural traditions are you a part of?
    • What was your last breakup like? [11]
    • How long should people date before meeting the family?
    • Have you ever been to therapy?
    • What’s the best way to communicate with you?
    • Would you rather live in the country or the city?
    • What do you think is more important: an emotional or physical connection?
Section 5 of 6:

Romantic Questions

  1. Open the conversation with a more suggestive question if you're feeling spicy. There’s nothing wrong with asking about his romantic wants and needs (especially if you’re already an item). [12] If you’re ready to get physical (or already have), ask him one of these spicy Qs:
    • What turns you on?
    • Have you ever been skinny dipping?
    • Do you like surprises?
    • What’s your favorite way to be woken up in the morning?
    • What’s something you’ve always wanted to try in bed?
    • Have you ever kissed someone under the mistletoe?
    • Do you like getting spicy texts?
    • What’s your favorite body part?
    • What romantic movie scene would you like to reenact?
    • What did you dream about last night?
    • What do you wear when you sleep?
    • Do you have a secret fantasy?
    • Have you ever had a threesome?
    • Do I show up in your dreams?
    • Is there anything you’ve ever wanted to teach me?
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Section 6 of 6:

Questions About You

  1. If you’re not sure what to ask, steer the conversation back to you. Center the question around something you want to know about yourself. In other words, what do you want to know about yourself from his perspective? This is a great way to learn about how he sees you and the relationship. Don’t be afraid to ask something like:
    • What song makes you think of me?
    • What was your first impression of me?
    • Do I remind you of anyone?
    • How would you describe me in 1 word?
    • Do you smile when you think of me?
    • If I was a flower, what type of flower would I be?
    • What color do you think I look best in?
    • What do you like most about me?
    • How do you feel around me?
    • Do you trust me?

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      References

      1. ↑ https://www.berkeleywellbeing.com/deep-questions-to-ask.html
      2. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      3. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      4. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      5. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      6. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      7. ↑ https://www.berkeleywellbeing.com/deep-questions-to-ask.html
      8. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      9. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      1. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      2. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
      3. ↑ Courtney Quinlan. Matchmaker & Dating Coach. Expert Interview
      4. ↑ Courtney Quinlan. Matchmaker & Dating Coach. Expert Interview

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