Learn More About Your Next BF By Asking Him These Questions

When you’ve set your sights on a new man, you want to learn everything about him, from his favorite food to his childhood pet’s name to his go-to karaoke song. If you’re in the exciting, early stages of getting to know someone, you might be wondering: what are some good, creative questions that will guarantee you get the answers you need? Keep reading for a comprehensive list of potential questions to ask your crush, with expert advice from professional matchmakers and dating coaches.

Great Questions to Ask a Guy Before Dating

Matchmaker April Davis explains that asking your guy crush questions and truly listening to his answers is key, as it demonstrates genuine curiosity about who he is. Ask him questions about his life, hobbies, values, and family, as well as what we wants from a relationship to see how compatible the two of you will be.

Section 1 of 10:

Basic Questions

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Ask him all about his preferences and pastimes. Although you may want to immediately dive into the deep end when getting to know your new potential man, it might be best to start by establishing the basics. Don’t underestimate the benefits of learning all his favorites, because each piece of the puzzle—no matter how seemingly small—leads to the big picture. Learn what makes him tick by asking the following questions:^{[1]
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- What’s your favorite movie? Least favorite?
- If you could meet any one of your heroes, which one would you choose?
- What fictional character do you wish were real?
- What’s your favorite color?
- Do you drink tea or coffee?
- What’s your favorite animal?
- What celebrity would you like to switch places with?
- What superpower do you wish you had?
- What’s your favorite holiday?
- Do you have any hidden talents?
- What’s your favorite book?
- What would your last meal be?
- What food could you eat every day?
- What’s one song you could play on repeat?
- What’s your favorite condiment?
- What’s your signature dish to make?
- What’s the best pizza topping?
- What are your top three favorite TV shows of all time?
- What’s your favorite band?

Section 2 of 10:

Questions About Their Values

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Learn what he believes in. You and your partner don’t have to be perfectly aligned on everything, but it’s important to have a foundation of compatibility when it comes to the things that really matter, like religion and family planning. Professional matchmaker and dating coach Lauren Sanders says, "Ask them about their family history and where they come from. Ask about family goals, if they want to get married, or if they just want a life partner.” Ask these questions and more to better understand the core of who he is and how well you two fit together.^{[2]
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Lauren Sanders
Matchmaker & Dating Coach

Expert Interview}
- Do you want to get married one day?^{[3]
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- Do you want children?
- How would you want to raise your children?
- Are you religious?
- What do you think happens after we die?
- What kind of relationship do you have with your parents?
- Where do you stand politically?
- How have your views evolved over time?
- What do you think is unforgivable from a moral standpoint?
- Where do you see yourself in 5 years? 10?

Section 3 of 10:

Questions About Their Past

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Inquire about his most formative memories. Although you may be swooning over the present version of your crush, the events and choices from his past are what molded him into the man he is today. Matchmaker April Davis begins, "For example, if somebody shares that they competed in gymnastics, that tells you something about them.” She goes on to explain, “It's really important to listen to what they're saying and then just be genuinely curious about what it is that you made them who they are."^{[4]
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April Davis
Matchmaker

Expert Interview}
- What’s the best costume you’ve ever worn for Halloween?^{[5]
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- What did you want your job to be when you were a kid?
- What’s the best trip you’ve ever taken?
- What’s the most memorable concert you’ve been to?
- What’s your favorite childhood memory?
- Do you have any major life regrets thus far?
- Is there anything you would change about your childhood?
- What’s the biggest life lesson you’ve learned so far?
- How old were you when you had your first kiss?
- What age has been your favorite so far?
- What’s the best gift you’ve ever been given?
- What’s the best piece of advice you’ve ever been given?

Section 4 of 10:

Questions About Relationships

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Express that you’re curious about his experience and intentions. You may not want to hear all the nitty gritty details about his previous relationships, but learning a bit about his romantic past can help you understand him better. You also want to be sure that you’re on the same page about what you want. Davis encourages you to ask, “Are you looking for a long-term thing? Or are you just having fun and want to see where it goes?” Here are some more ideas:^{[6]
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April Davis
Matchmaker

Expert Interview}
- What are you like as a boyfriend?^{[7]
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- How do you define love?
- Do you consider yourself romantic?
- Where do you think the most romantic vacation would be?
- Do you believe in soul mates?
- What’s the longest relationship you’ve ever had?
- What’s the best date you’ve ever been on? The worst?
- Have you or would you ever stay friends with an ex?
- What’s your favorite part about being in a committed relationship?
- How long would you want to be dating before getting engaged?
- When did you first fall in love, and how did it feel?
- How did your first breakup go?
- How do you feel finances should be split in a long-term relationship?
- Do you think two people in a couple should also be best friends?
- Are there any aspects of your life that are off limits to your partner?
- Have you ever cheated or been cheated on?
- Do you think cheating is ever acceptable?
- Have you or would you ever stay with someone unfaithful?
- What’s a surefire way to keep you happy in a relationship?
- Are you healed from your past heartbreaks?

Section 5 of 10:

Questions to Gauge Compatibility

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Consider how well your goals and preferences align. If attraction is what hooks you, then compatibility is what reels you in. Your new beau may seem perfect on paper, but asking him the hard questions will guarantee that you’re making the right choices for yourself. Matchmaker and dating coach Courtney Quinlan says, “Ask about future goals in life like, ‘Where do you want to be in the next five years?’ You need to make sure that you’re aligned as far as what your goals are—are they similar? Or are they really far apart?" Read ahead for more options:^{[8]
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Courtney Quinlan
Matchmaker & Dating Coach

Expert Interview}
- What’s your preference on paying at the end of a date?^{[9]
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- Are you a morning person or a night owl?
- What does your ideal weekend look like?
- Are you a cat or a dog person?
- What’s your love language?
- What’s your biggest dating dealbreaker?
- How important is physical intimacy for you?
- What do your morning and bedtime routines look like?
- Would you consider yourself an adrenaline junkie?
- Are you more of an introvert or an extrovert?
- When you travel, do you like to have a packed itinerary or do you prefer a chill vibe with flexible plans?
- What is your relationship to alcohol?
- What do you struggle with the most in relationships?

Section 6 of 10:

Fun and Flirty Questions to Ask Him

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Put a smile on his face with silly and suggestive questions. Questions aren’t just to collect intel, they can help spice things up, too! Asking flirty questions can serve as a kind of foreplay, allowing you to begin fantasizing about the future of your relationship. Have fun when you flirt—being silly and playful is totally allowed! Plus, you get to see their silly side, too!^{[10]
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- What do you find most attractive about me?
- When was the last time you felt butterflies?
- What’s a pick-up line you would use on me?
- Have you ever fantasized about me?
- What’s on your sexual bucket list?
- Do you have a type? Am I it?
- Do you like it when a girl makes the first move?
- What do you find to be the sexiest part of a person’s body?
- How would you seduce me?
- What’s the best compliment you’ve ever received?

Section 7 of 10:

Serious and Profound Questions to Ask Him

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Go deeper into the things that really matter. If you’ve already covered the basics, relationship history, and compatibility, it’s time to ask the hard-hitting, thought-provoking questions. These may require more careful consideration and longer responses, but his answers should give you the clarity you need about the kind of man and person he is. Find out if he’s the one for you by asking some— or all— of the following:
- Which skill would you choose if you knew you could master it in a year?
- What’s something illegal that you think should be legal?
- Do you remember your dreams? Any recurring ones?
- What’s your biggest fear?
- What does being a man mean to you?
- What’s the scariest thing you’ve ever done?
- Have you ever had a near-death experience?
- How do you hope to be remembered?
- When was the last time you cried?
- Which villain do you think is most misunderstood?
- What is something everyone always gets wrong about you?
- What is something you think everyone should experience at least once in their life?
- Who is your best friend and why?
- Do you want to be more or less like your parents?
- How would you describe yourself in three words?
- What’s your favorite quality about yourself?
- Who is your favorite family member?
- Have you ever been betrayed by a friend?
- What three songs would be featured on the soundtrack to your life?
- What’s the meaning of life?

Section 8 of 10:

Funny Questions to Ask Him

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Make him giggle with these hilarious head-scratchers. They that laughter is the best medicine, but it could also be the key to getting to know your special guy better! Not only will you learn more about him, but these questions will give him a chance to show you his sense of humor, which can certainly nudge the budding romance forward. A little back-and-forth banter is an excellent way to build chemistry, just like they do in the rom-coms!^{[11]
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- If you could switch bodies with the president or your favourite actor, which would you choose?
- If you could be an airplane or a train, which would you choose?
- Would you rather wear the same socks for a month or the same underwear for a week?
- What’s the worst text you’ve accidentally sent?
- Who is your favourite comedian?
- Is cereal soup?
- Would you rather watch nothing but Hallmark Christmas movies or horror movies?
- If you were an inanimate object, what would you be?
- Is a hot dog a sandwich?
- Would you rather give up your cellphone for a month or not shower for a month?
- What would be the worst “buy one, get one” sale item of all time?
- What would three of your cheat codes be if life were a video game?
- Would you rather have a magic carpet or a crystal ball?
- What kind of secret society would you start?
- What’s the most embarrassing thing in your closet?
- Would you rather have teeth for hair or hair for teeth?
- What’s the best inside joke you’ve ever been a part of?
- If all animals could talk, which one do you think would be the rudest? How about the funniest?
- What’s the current name of your WiFi?
- Would you rather eat chocolate-flavored broccoli or broccoli-flavored chocolate?
- What’s the most useless invention of all time?
- What’s the worst pizza topping?
- Would you rather have a pet penguin or a pet panda?
- What’s one thing everyone looks stupid doing?
- What’s the best type of cheese?
- Would you rather have a third nipple or an extra toe?
- What’s the funniest insult you can come up with on the spot?
- What mythical creature do you wish were real?
- Would you rather live on a desert island with your celebrity crush or in a mansion with your ex?

Section 9 of 10:

Random Questions to Ask Him

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Take him for a spin with these questions out of left field. Keep your man on his toes with random questions out of the blue. You can try texting him throughout the day with a ridiculous “would-you-rather” scenario, inquire about his favorite meme, or ask him which form of potato is the best. If he answers your random questions with humor and kindness, he might be a keeper!^{[12]
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- If I were a flower, what kind of flower would I be?
- What do you most often think about before you fall asleep?
- What puts you in a good mood?
- What’s your ideal night in?
- Would you rather give or receive a gift?
- What’s the most surprising thing about you?
- If you could be any insect, which one would you choose?
- What’s your favorite way to eat a potato?
- If you could only wear one color for the rest of your life, which one and why?
- Are you a night owl or an early bird?
- How would you spend one million dollars?
- What does your dream house look like?
- If you could be a professional in any sport, which would you choose?
- What’s your go-to joke?
- Do you have a favourite meme?
- What’s your comfort film?
- Did your family practice any unique holiday traditions?
- If you could travel forward in time or backward in time, which would you choose?
- You can attend a concert by any musician alive or dead—who do you choose?
- Which is worse, to be sweaty or cold?
- Sneakers or sandals?
- Would you rather write a bestselling book or paint a famous piece of artwork?

Section 10 of 10:

What to Consider when Asking Questions

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1
Avoid interrogating your crush. It may seem tempting to fire off all of your questions one by one, machine gun style. However, this could overwhelm him or make him feel like he’s interviewing for a job. Instead, try to seamlessly weave your questions into conversation. It will feel more organic and more likely to elicit an honest, unrehearsed answer.
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Pay close attention and genuinely listen to his answers. Don’t just ask questions to say you did. Give him your undivided attention, listen intently, and truly absorb what he has to say. If you’re confused about anything, repeat his answer back to him and ask for clarity. He’ll appreciate how thoughtful and intentional you are about learning about him.^{[13]
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Expect the questions to be reciprocated. Just as much as you want to get to know him better, he probably wants to learn just as much about you! Ask your crush questions, from silly to salacious, but be prepared to share your own answers with him in turn, as many of his replies may be concluded with, “And how about you?” You have a slight advantage, though, as you’ll know what questions to ask ahead of time and can have some ideas already brewing. Well done, you!