200 Fun, Flirty, & Deep Questions to Get to Know a Guy Better

Trying to learn more about a guy and deepen your connection? Asking engaging questions is the best way to bond with someone, whether you’re chatting over text or in person. In this article, we’re providing the ultimate list of fun, flirty, and interesting questions to ask a guy to get to know him better. We also talked to dating experts Lauren Sanders and Laura Bilotta for tips to break the ice and deal with social anxiety while dating.

Best Questions to Ask a Guy When Getting to Know Him

What’s your death row meal?
What brings out your inner child?
What’s your favorite way to unwind?
What’s one thing on your bucket list?
What was your first impression of me?
Would you rather have more time or more money?
What’s the best piece of advice you’ve ever received?

Section 1 of 7:

Fun Questions to Get to Know a Guy

Download Article

Break the ice with these fun and easy conversation starters. To avoid sounding like a job interview, rephrase classic icebreakers in an engaging way. Ask open-ended questions that help you learn more about your crush, while keeping the conversation fun and lighthearted. Some topics you can talk about include his personality, hobbies, interests, and tastes:
- What’s your dream job?
- What’s your zodiac sign?
- Who’s your favorite artist?
- Who’s your celebrity crush?
- What’s your favorite season?
- What’s your death row meal?
- What’s your favorite dinosaur?
- What’s your go-to coffee order?
- What could you write a book on?
- Do you have any hidden talents?
- What was your last Netflix binge?
- Are you introverted or extroverted?
- What’s your favorite way to unwind?
- Are you an early bird or a night owl?
- What’s one thing on your bucket list?
- What’s your favorite outdoor activity?
- What’s the best character of all time?
- What’s your most prized possession?
- What’s the greatest movie of all time?
- What does your perfect day look like?
- What song can you never get sick of?
- Do you prefer staying in or going out?
- What’s one thing you can’t live without?
- What are 3 things that make you happy?
- What’s your dream vacation destination?
- What’s the most-used app on your phone?
- How do you usually spend your weekends?
- What’s something you’re looking forward to?
- What’s the best concert you’ve ever been to?
- What’s something you’ve always wanted to learn or try?
- If you could have any superpower, what would you pick?
- If you won the lottery, what’s the first thing you would buy?
- If you had a time machine, which decade are you traveling to?
- What’s the most interesting thing you’ve seen or read this week?
- If you could live in any fictional world, which one would you choose?
- If you could have dinner with 3 people, dead or alive, who would they be?

Section 2 of 7:

Funny Questions to Get to Know a Guy

Download Article

Throw out a silly question to bond and make him laugh. Sharing a laugh with someone is proven to strengthen relationships.^{[1]
X
Trustworthy Source

Greater Good Magazine
Journal published by UC Berkeley's Greater Good Science Center, which uses scientific research to promote happier living

Go to source} So, come up with an unexpectedly goofy question to get the giggles going. “Joking around with a guy is a great way to build rapport and show that you’re interested in getting to know him better,” according to Bilotta. ^{[2]
X
Expert Source

Laura Bilotta
Dating Coach & Matchmaker

Expert Interview}
- What gives you the ick?
- Is a hot dog a sandwich?
- What’s your favorite meme?
- Who’s your favorite comedian?
- What’s your most useless skill?
- Is Die Hard a Christmas movie?
- What would you be arrested for?
- What’s your favorite Shrek movie?
- What’s your biggest irrational fear?
- What’s the worst movie of all time?
- What’s your favorite form of potato?
- Where do you want to be in an hour?
- What would you do during the Purge?
- What’s your idea of the perfect burger?
- What’s one food that should be banned?
- What’s the best prank you’ve ever pulled?
- What kind of secret society would you start?
- What’s one fact you wish you could unlearn?
- What’s one thing everyone looks stupid doing?
- What’s the worst text you’ve accidentally sent?
- What’s the most embarrassing thing in your room?
- 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?
- What celebrity would be the worst leader of our country?
- What inanimate object would you delete from existence?
- What’s an embarrassing song or band you secretly love?
- What’s the weirdest thing you’ve seen in someone’s house?
- What’s the best excuse you’ve given to skip school or work?
- If you had to fight a historical figure, who would you choose?
- How long do you think you’d survive in a zombie apocalypse?
- What’s the most savage insult you can come up with on the spot?
- What’s the most unnecessary white lie you’ve ever told someone?
- When’s the most inappropriate time you’ve laughed at something?
- In those first few seconds, are you hoping it’s “Ice Ice Baby” or “Under Pressure?”

Section 3 of 7:

Flirty Questions to Get to Know a Guy

Download Article

Get his heart racing with these fun and flirty questions. Trying to take your relationship to the next level? Ask some flirty questions to create tension and drop hints that you’re interested! Finding out his turn-ons, usual type, and relationship goals can also help you decide if you’re a good match.
- What’s your toxic trait?
- What’s your usual type?
- When was your first kiss?
- What do you wear to bed?
- What’s your love language?
- What’s your biggest turn-on?
- Do you believe in soulmates?
- What’s your best pick-up line?
- Do you develop crushes easily?
- What song gets you in the mood?
- What do your friends think of me?
- Do you prefer kissing or cuddling?
- Do you think you’re a good kisser?
- What was your sexual awakening?
- Would you ever go skinny dipping?
- Do you consider yourself romantic?
- What’s your biggest guilty pleasure?
- Have you ever fantasized about me?
- What’s your favorite thing about me?
- What was your first impression of me?
- What traits do you look for in a partner?
- When’s the last time you felt butterflies?
- What’s your idea of the perfect first date?
- What’s the best movie to watch on a date?
- What’s something that reminds you of me?
- What’s the most attractive physical feature?
- What are your green flags in a relationship?
- What’s the hottest thing a girl could text you?
- If you were me for a day, what would you do?
- Do you prefer being single or in a relationship?
- Do you like it when a girl makes the first move?
- How do you know when you’re really into someone?
- Do you prefer being the big spoon or the little spoon?
- If we formed a band, what kind of music would we make?
- What’s the first thing that comes to mind when you think of me?

Section 4 of 7:

Interesting Questions to Get to Know a Guy

Download Article

Drop a “would you rather” style question to lighten the mood. If you want to take the conversation to the next level, ask a hypothetical question to catch him off guard! These unique and thought-provoking scenarios are perfect for learning more about his personality, whether you’re talking in person or over text:
- Would you rather give up salt or sugar?
- Would you rather be too hot or too cold?
- Would you rather be bald or have no eyebrows?
- Would you rather be able to control water or fire?
- Would you rather explore space or the deep sea?
- Would you rather have more time or more money?
- Would you rather always shout or always whisper?
- Would you rather never age physically or mentally?
- Would you rather never sing or never dance again?
- Would you never have a home or never go outside?
- Would you rather save 5 loved ones or 1,000 strangers?
- Would you rather never see your friends or family again?
- Would you rather live next to a huge stadium or the airport?
- Would you rather be half your height or double your weight?
- Would you rather have a pause or rewind button in your life?
- Would you rather lose the ability to speak or the ability to read?
- Would you rather be the funniest or smartest person in the room?
- Would you rather be granted one huge wish or 100 small wishes?
- Would you rather be one hour late or one hour early to everything?
- Would you rather have no one show up at your wedding or funeral?
- Would you rather always be stressed and busy or always be bored?
- Would you rather be stronger than average or smarter than average?
- Would you rather live in a world where there’s no crime or no privacy?
- Would you rather have your first child when you’re 18 or 50 years old?
- Would you rather always have a full phone battery or a full tank of gas?
- Would you rather not be able to buy coffee or order takeout for a month?
- Would you rather know the date of your death or the cause of your death?
- Would you rather marry the person of your dreams or have the job of your dreams?
- Would you rather speak every language in the world or be able to speak to animals?
- Would you rather get a million dollars right now or $100,000 every year for 10 years?
- Would you rather lose a finger or have a headache every day for the rest of your life?
- Would you rather take back anything you say or hear any conversation that’s about you?
- Would you rather never be able to go out during the day or never be able to go out at night?
- Would you rather have eyes that can film everything or ears that can record everything?
- Would you rather be more attractive than your partner or have your partner be more attractive than you?
- Would you rather have everyone be able to read your mind or everyone you know have access to your search history?
- Would you rather be famous when you’re alive and forgotten after death, or unknown when you’re alive and famous after death?

Section 5 of 7:

Personal Questions to Get to Know a Guy

Download Article

Delve into deeper questions to see if your values align. According to Sanders, you should “ask them about their family history and where they come from, what they’re searching for in a relationship, [their] family goals, and spiritual affiliation.”^{[3]
X
Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} These topics can be touchy for some guys, so make sure to ask him if it’s okay first. Otherwise, it’s a great way to learn about his beliefs and character, plus build intimacy and trust in your relationship.
- Who’s your role model?
- What’s your biggest fear?
- Do you have any regrets?
- What’s your top goal in life?
- Where is your happy place?
- Are you close to your family?
- Are you spiritual or religious?
- Do you want kids in the future?
- What are you most grateful for?
- What brings out your inner child?
- How do you feel about marriage?
- Do you believe in fate or free will?
- What’s your definition of success?
- Do you believe in second chances?
- What makes you smile on a bad day?
- Who would you call in an emergency?
- Where do you see yourself in 5 years?
- What’s your favorite childhood memory?
- Do you think money can buy happiness?
- Do you care what people think about you?
- How do you know you can trust someone?
- What are 3 things you love about yourself?
- What’s one thing no one knows about you?
- What role do you play in your friend group?
- What’s the scariest thing you’ve ever done?
- What’s the biggest misconception about you?
- How do you handle conflict in your personal life?
- What are your non-negotiables in a relationship?
- Do you think physical or emotional pain is worse?
- What did you want to be when you were younger?
- What’s one thing you would change about yourself?
- What’s the best piece of advice you’ve ever received?
- Do you think it’s okay to tell white lies in a relationship?
- What social or political issues are most important to you?
- What’s the most important life lesson you’ve learned so far?
- What’s one thing you would do if you knew you could not fail?
- If your life was a book, what’s the title of the chapter you’re in now?

Section 6 of 7:

Random Questions to Get to Know a Guy

Download Article

If you’re not sure where to start, ask your guy these random questions. Once you’ve covered the basics of jobs, dreams, hobbies, family, etc., you may want to delve a little deeper without getting too deep. If you want to continue chatting with your crush but aren’t sure what to talk about, start getting to know each other’s more difficult-to-uncover quirks with this mix of funny and thought-provoking random questions.
- Sneakers or sandals?
- What’s your ideal breakfast?
- Driver’s seat or passenger seat?
- What’s your go-to karaoke song?
- Do you always remember your dreams?
- What would your dream house look like?
- How would you spend one million dollars?
- Who would narrate a book about your life?
- Which condiment makes every food better?
- What’s the funniest text you’ve ever gotten?
- What’s the most interesting fact that you know?
- If you could be any insect, which one would you be?
- What's the most spontaneous thing you've ever done?
- If you could live in any era, which one would you choose?
- If you could represent any sport in the Olympics, what would it be?
- If you had to describe yourself in three words, what would they be?
- Would you rather write a bestselling book or record a chart-topping song?
- If you could trade places with any Marvel character, which one would you choose?
- If you could only wear one color for the rest of your life, which one would you choose?
- Ice cream every night for a month or the best pizza in the world every week for a year?

Section 7 of 7:

Frequently Asked Questions

Download Article

1
How can I tell if a guy likes me? According to Sanders, “[he might] ask questions about your life” or "offer to do things for you.”^{[4]
X
Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} This includes helping you with an assignment, buying you a coffee, or offering to run an errand on your behalf. Other signs that your crush likes you include:^{[5]
X
Research source}
- He mirrors your behavior.
- He smiles a lot around you.
- He initiates physical contact.
- He teases or compliments you.
- He remembers small details about you.
- He finds excuses to spend time with you.
- He makes frequent and prolonged eye contact.
2
How can I deal with social anxiety while dating? Bilotta says to “make it a priority to ask questions and be curious about your date.”^{[6]
X
Expert Source

Laura Bilotta
Dating Coach & Matchmaker

Expert Interview} Practice active listening and ask follow-up questions to show that you were paying attention to the other person. Preparing a list of 4-5 icebreakers can also help ease your anxiety and start an engaging conversation.
- If you’re super anxious on a date, don’t be afraid to admit it! You could say, “I’m feeling a little nervous because you’re so cute.”
According to Sanders, “you have good compatibility if you share common interests, values, and life goals [with them].”^{[7]
X
Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Other signs of relationship compatibility include: having strong communication skills with your crush, sharing a similar desire for independence, being physically attracted to one another, sharing similar religious or spiritual beliefs, and matching the same level of extroversion or introversion.^{[8]
X
Research source}
According to Bilotta, some of the top icebreakers are “pets, hobbies, or something that may be relatable to you.” She also says “it’s important to ask open-ended questions that leave room for more than a yes or no answer.”^{[9]
X
Expert Source

Laura Bilotta
Dating Coach

Expert Interview} Simply put, find common interests with your crush and ask open-ended questions to keep the conversation going.

Join the Discussion...

What are some good questions to ask a guy?

Kristina Mirgorodskaya
Dating Expert

When you're wondering what questions to ask a guy you like, ask him about his biggest dreams, what he wants to achieve in life, or what’s important for him in a relationship. Try to be creative with your questions and responses by commenting on specific things he's talked about.