Epic List of Questions to Ask a Guy (300+ to Use)

Looking for the best questions to ask a guy? Are you talking to your crush? Did you just meet someone new online and you like him very much? The talking and dating stage can be quite exciting, especially when there is intense chemistry between the two of you. But as a woman, it can be challenging to carry on the conversations sometimes.

Disclaimer: If you’re struggling to make connections with others and are feeling like this is a serious problem, it can be beneficial to seek the help of a licensed therapist, counselor, or life coach. For a good resource, visit the Mental Health America’s list.

Best Questions to Ask a Guy

What does ‘I Love You’ mean to you?
Do you believe in soulmates?
What did you major in back in college?
Which achievement in your life are you most proud of?
Are you someone who talks a lot about their feelings?
What are your thoughts on toxic masculinity?
What’s your favorite song?
What do you think your best physical feature is?
What’s your biggest guilty pleasure on a Sunday night?
Are you secure in your masculinity?
Which gender stereotype annoys you the most?
What would you say is your greatest strength and weakness?
Do you believe in gender-specific roles?
What is the most important factor in a relationship?
Do you entertain the idea of having a polygamous relationship?
How do you differentiate love from obsession?
What is the best compliment that you have ever received?
Does the idea of love bombing scare you?
Which characteristic trait in women are you most fond of?
Which historical figure do you appreciate the most?
Who is your favorite cartoon character?
Are you a competitive person?
Do you like small talk?
Are you an introvert, extrovert, or an ambivert?
What’s something you stressed over but never became a big deal in your life?
What is your bucket list for this year?
Do you have an easy time being friends with the same or opposite gender?

Good Questions to Ask a Guy

Which childhood memory are you most fond of?
What is your love language?
Do you have doubts about yourself? Can you tell me about them?
What turns you off in a person?
How do you lose respect for someone?
Can you tell me about a movie that best reflects your life?
Do you have a nickname?
Tell me about your arch-nemesis.
Do you have a secret talent? If so, then what is it?
What is the best and worst thing about being a man?
Are you a trivia person?
What is that one thing that most people mistake you for?
If you were given a million dollars, what is the first thing that you would do?
Do you enjoy surprises?
What are you most grateful for in life?
Can you tell me about the best phase in your life?

Expert dating advice: Melissa Divaris Thompson (LMFT suggests that women should get to know themselves. Know your must-haves and what deal-breakers you care about. It’s the best way to be clear about what a suitable relationship looks like for you before engaging.

Flirty Questions to Ask a Guy

How would you react if I kissed you right now?
What turns you on most in women?
Can you tell me about your first kiss?
What is your biggest turn-off in a girl?
Are you a kisser or a cuddler?
Would you be interested in cuddling with me right now?
Can you spoon me?
Tell me about your first teacher crush.
How on earth are you still single?
What is your secret fantasy?
Do you have a pet name for me?
What is going through your mind right now?
Can you share your Spotify playlist with me?
Do you have a song for me?
Does any song remind you of me?
So, when are we sharing our mixtapes?
Would you be willing to let me have the last bite of the pizza?

Questions to Ask a Guy Over Text

Name some of your favorite movies.
Could you suggest some of your favorite TV shows to watch?
What are you doing this weekend?
How does your weekend usually go?
Have you been to a concert lately?
Do you have any hidden talents that I should know of?
Describe yourself in one word.
Can you tell me about one of your most memorable experiences?
Did anything weird happen to you this week?
What is that one random thing you recently purchased from the internet?
Can you name some of your pet peeves?
Are you a dog or cat person?
Do you enjoy having pets around?
Name some of your dream destinations.
What is your favorite dish?
What is your go-to snack?
Narrate to me a favorite childhood experience of yours.
Which superpower would you want to have?
What are your thoughts on sharing social media passwords with your significant other?

Deep Questions to Ask a Guy

Is there anything you’d like to change about yourself?
What is your biggest motivation?
Do you have any regrets in life?
Are you someone who’s driven by emotions?
Do you make your decisions based on emotions or logic?
What is the most fascinating thing about your career right now?
Are you comfortable telling me about your biggest fear?
What is your family most proud of?
Can you tell me about the most precious gift you have received so far?
What ticks you off the most?
How would your family and friends describe you?
Where do you see yourself a couple of years from now?
What is the one thing you miss most about being a child?
What was it like growing up in your town?
Do you enjoy politics? What are your thoughts?
Would you ever take back someone who cheated on you?
What are your thoughts on open relationships?
Are you happy with your life right now?
What is the deal breaker for you in relationships?

Personal Questions to Ask a Guy

Who did you look up to growing up?
Did you have a good childhood?
What was your aim in life growing up?
Who in your family are you closest to?
Do you still go to family gatherings?
What are you most afraid of?
Which behavior or habit did you have a hard time getting rid of?
Are you a religious or a spiritual person?
How was your environment growing up?
Do you have any resentment towards anyone growing up?
What did your biggest heartbreak teach you?
Can you name that one song that summarizes your life?
What are your biggest insecurities?
When did you have your first kiss?
How did your first kiss feel like?
What quality in yourself are you most proud of?
Do you have anything that you wish to change about yourself?
Would you be open to telling me your biggest secret?
Are you someone who puts conditions in love?
Do you have any regrets about how you treated someone?
What is the biggest lesson you have learned from your past relationships?
Do you have any regrets about your past relationships?

Expert advice: Anna Yam, Ph.D., from Bloom Psychology suggests that even if you’re starting a new relationship or trying to build one, don’t lose focus on yourself. Your own interests. And think long-term about adding a new relationship into those things.

Funny Questions to Ask a Guy

Are you skilled when it comes to flirting?
Do you have any special techniques for flirting?
Name your biggest celebrity crush.
Which movie character do you want to play?
Do you like pineapple on a pizza?
What is the most embarrassing or humiliating thing in your search history?
Do you think that you will be able to survive a zombie apocalypse?
What is your most useless talent?
How would you handle a no-internet day?
Can you tell me about your most annoying habit?
Narrate me a conspiracy theory that you have.
What is the funniest lie that you said to avoid getting scolded by your mom?
Do you have a funny joke in your mind right now?
Which job best suits you post-apocalypse?
Did the chicken or egg come first?
Tell me something about you that I would have a hard time believing.
Show me your best face when you are in a room with people you don’t like.
What is your spirit animal?

Interesting Questions to Ask a Guy

Do you have any fear? If so, then what is it?
What makes you have a good laugh?
Can you tell me about the scariest thing that you have ever done?
Name some things in your life that you are most grateful for right now.
What is the biggest motivating factor behind your life?
Are you a morning person or a night person?
Who was your first kiss? Was it with your first crush?
If you had three wishes, what would they be?
Which movie would you have no problem watching for the rest of your life?
Tell me something that you have never told anyone before.
What is one thing that you have done that you will never do again?
Hit me with your best joke.
Do you have any stupid memory that you would like to share?
What physical characteristics are you most proud of in yourself?
Do you wish you could rewrite your past sometimes?
What’s your favorite childhood memory?
If you could have any dream job, what would it be?
What’s your favorite physical feature of a woman?
What is your most expensive habit?
What’s one thing you wish to change about your past?
Who do you confide in when you are burdened with problems?
What is that one meal that you will never get tired of?
If today were your last day on earth, what would you do?
Can you describe yourself in three words?
How do people usually perceive you at first?
Describe your ideal date night,
Name 3 of your favorite go-to drinks.
What do you want to do before you leave this earth?

Weird Questions to Ask a Guy

Would you want to be reincarnated as a dog or cat?
How long does it usually take to make your favorite dish?
Do you have any abnormalities?
How many hearts did you break up till now?
Do you want 10 children or 10 wives?
Which insect are you most scared of?
Do you fantasize about your partner cheating on you?
Have you ever walked in on your parents?
How many lies did you tell today?
Can you guess the number of guys I have kissed?
Do you change your boxers every day?
Have you ever swallowed your vomit?
How many times do you fart in a day?
If you were given 50,000 Dollars, would you kiss another guy?
Are you someone who pees when they shower?
Have you ever made a move on your best friend’s girl?
When are you going to ask me out?
Do you want to get married to me?
Are you someone who asks for directions when they are lost?
Would you go on 2 dates in the same day?
Do you enjoy farting in elevators?
Have you ever created a fake profile on Instagram?
What would you do if you woke up as Captain America for a day?

Fun Questions to Ask a Guy

What is the most unusual place that you have ever been to?
Do you enjoy cooking?
Are you an outdoorsy person?
Do you have any recent resentments on something that you paid for?
Is there any date that you regret going to?
What one meal can you eat for the rest of your life?
What do you think of blind dates?
Are you into astrology?
What do you think of astrology?
Do you believe in destiny or hard work?
What is your astrological sign?
How do you usually end your day?
What are you most passionate about?
Are you someone who plans things in advance or a spontaneous person?
Can you tell me about the first 3 things on your bucket list?
What is your favorite movie?
Do you have a favorite romance movie?
What is the scariest flick that you have ever seen?
How do you compose yourself in serious situations?
What was the first phone you owned?
Do you believe in communication or sweeping things under the rug?
What about the opposite gender attracts you?
Are you the jealous type?
Did you watch Twilight? Care to share your thoughts?
What is your favorite ice cream flavor?

Serious Questions to Ask a Guy

How long did your longest relationship last?
Why did you break up with your ex?
Do you wish to have children someday?
What do you think about live-in relationships?
Are you an ally of the LGBTQ+ community?
Do you believe in Gay rights?
Are you a feminist?
What do you consider feminism to be?
Do you believe in the supernatural?
Would weight gain and aging lessen your attraction toward your partner?
Should age be a factor when it comes to voting?
What qualities are you looking for in the next President?
Are you someone who holds grudges?
Do you have any addiction?
Were you physically or emotionally abused growing up?
Is infidelity a deal breaker for you in relationships?
Have you ever been unfaithful in your previous relationships?
Would you tell your partner if you ever made the mistake of cheating?
What is the best advice that you have ever received?
How do you usually deal with challenges?

Freaky Questions to Ask a Guy

Do you enjoy getting massaged?
Which is your favorite area to be massaged?
Can you tell me about your fetish?
Do you have any weird fetish that no one knows about?
Are you planning to be naughty or nice this Christmas?
Tell me about your best make-out session.
Would you like the idea of meeting up?
Can you tell me about your best bedroom experience?
What are your thoughts on one-night stands?
Do you enjoy “dirty talk” from time to time?
What is your biggest turn-off in the bedroom?
Do you have any friends with benefits?
What is the freakiest thing someone’s ever said to you?
Tell me about your wildest fantasy.
Are you someone who enjoys foreplay?
How long have you gone without doing it?
Do you enjoy getting kissed on your neck?
Are you a dominant or submissive person?

Awkward Questions to Ask a Guy

Were your exes crazy?
Are you a virgin?
Do you like picking your nose?
How much money do you make?
Can you tell me about your family’s wealth?
Did you cry recently?
Tell me something you did in the previous relationship that you regret.
Do you have any weird guilty pleasures that I should know of?
How much do you currently weigh?
Did you ever pee in the pool?
Do you enjoy licking your plate after dinner?
Are there a lot of girls’ numbers in your phone?
What caused you to break up with your last girlfriend?
Do you fantasize about cheating when you are in a relationship?
Have you ever fantasized about being in a relationship with a man?
Are you insecure?
Do your underarms smell after a workout?
Do you brush your teeth often?
Have you ever tasted your own booger?
Did you practice kissing the mirror growing up?
Do you have feet odor?
What is the most unattractive part of your body?
Show me the last text that you sent.

Truth or Dare Questions to Ask a Guy

Truth

What is the worst thing that you have ever done?
Tell us your biggest insecurity and why.
When did you last lie?
What is your darkest secret?
Have you ever cheated on your girlfriend?
What is that one thing you never want your family to know?
Give us your honest opinion on polyamory.
Can you tell us about your worst drunken experience?
What is the most disgusting thing that you have secretly done?
Why did you really break up with your last girlfriend?
Who would you kiss in this room right now?
Do you have a crush on anyone in this room?
Have you lied at least once in this game so far?

Dare

Show us your most embarrassing picture.
Reveal the last 3 people you texted, along with their messages.
Give us your Instagram account to DM a girl from your following.
We challenge you to do 100 push-ups.
Eat a spoonful of cinnamon.
Show us your passport picture.
Give us your best twerking moves.
Tell us about the most humiliating moment of your life.
Give us your best lap dance.
Do the chubby bunny challenge with this marshmallow.
Give us your best John Wick impression.
Reenact a scene from your favorite movie.
Call your brother and tell him that you love him in a cheesy way.

Intimate Questions to Ask a Guy

What quality in me attracted you to me the most?
Do you have any questions that you refrained from asking me in the past?
When did you know that you were falling in love?
How do you want me to best show you love?
When do you feel the most loved?
Is there anything that you wish to unlearn about yourself?
Are you happy in this relationship?
Describe your perfect date.
When was the last time you cried?
What would you say to your younger self if you had the chance?
Have you ever felt proud of me?
Is there anything you want me to do to better our relationship?
What do you enjoy most about our relationship?
Name a movie that best reflects our bond.
Tell me your favorite memory of this relationship.
Do I make you happy?
Is there anything that I am doing that’s hurting you?
When do you feel the closest with me?
Are you ready to compromise in relationships or is it asking too much?
Which destructive habit are you most scared of?

Hard Questions to Ask a Guy

Are you more into brains or looks?
When is the right time for two people to get married?
How do you handle things when you lose a loved one?
Do you want to be cheered up or left alone when you are in a bad mood?
Would you consider relocating for love?
What is the hardest thing you had to unlearn about yourself?
Are you someone who judges others before knowing them?
Would you change your spiritual beliefs for someone you love?
How would you handle your family not liking your partner?
Are you a confrontational person?
Do you usually stay in touch with your exes?
How do you see yourself in the next 5 years?
Would you end a relationship if your parents disapproved it?
Thoughts on privacy in relationships?
Can you make long-distance relationships work?
Do you see a future with me?
Will you ever be able to quit alcohol?
What are your thoughts on being vegan?
Which belief did you have a hard time getting rid of?

Embarrassing Questions to Ask a Guy

How long does it take for you to get ready for a date?
Do you want me to give you a makeover?
Name one reason for which you will probably get arrested for.
Have you ever considered getting plastic surgery?
How many women have you been physically intimate with?
Do you know that you resemble a lot to my ex-boyfriend?
Are you someone with a lot of debt?
Have you ever lied about anything in your job interview?
When did you lose your virginity?
Do you enjoy being friend zoned?
Can you tell me about your dumbest memory from college?
Have you ever been arrested before?
Do you have enough money to pay for our date?
What is the most embarrassing thing that’s ever happened to you?
Have you ever lied in your resume?
Can you show me your bank balance?
Does this dress make me look fat?
Do you suffer from any STDs?
What is the most ridiculous advice you ever gave for being late at work?
Can you think of the cheesiest thing you have ever done for a girl?

Cute Questions to Ask a Guy

What are you looking for in a woman?
Are you a ticklish person?
Do you want to share any of your family traditions?
Have you gotten into any trouble with your parents lately?
Can you tell me how you were in school?
What is your favorite Thanksgiving meal?
Does the idea of spontaneous dating excite you?
What is next on your bucket list to fulfill?
Are you more of a beer or wine guy?
Have you told your loved ones about us yet?
Where are you going to take me on our first date?
Who is the first family member you would introduce me to?
Are you a dog person or a cat person?
If you spend money, what do you spend it on?
Who is your best friend?
If you could eat one food for the rest of your life, what would it be and why?
What was that one thing you noticed about me first?
Have you been working out lately?
Thoughts on PDA?
If the world was ending, you would come over, right?
How do you want people to remember you?
Does emotional maturity resonate with you?
How do you know she’s the one?
When was the last time you cried while watching a movie?
What is the best compliment that you have ever received?

Spicy Questions to Ask a Guy

Have I ever been in your dreams?
Do I make you nervous?
How do you usually spice things up in a relationship?
Can you name the first thing that you noticed about me?
Which body part of yourself are you most proud of?
Do you prefer curves or athletic build in girls?
Have you ever fantasized about me?
Am I the girl of your dreams?
Do you recall any intense make-out memory?
How does it feel when our lips touch?
Do you get jealous when other men hit on me?
Does my sight make you nervous?
Are you a bibliophile?
Have you ever cooked breakfast for your date after making love?

Important Questions to Ask a Guy

Is jealousy healthy in a relationship?
Do you regret cheating on your girlfriend?
Are you vocal about the way you feel, or do you bottle them up?
Is money a concern to you?
Do you think it’s important for couples to be financially literate nowadays?
What is secure masculinity to you?
Does the idea of instant physical gratification appeal to you?
Is porn destroying or helping the current generation in viewing sex?
How do you balance your work and personal life?
Are you enjoying your current job?
Name one social issue that you are extremely passionate about.
How do you define a stable relationship?
What is the most important element in long-term relationships?
Are you good with conflict resolutions?
What is that one thing that you wish most people knew about you?
Are you a dismissive person?
What is your attachment style in relationships?
Do you believe in texting and calling your partner incessantly?

Risky Questions to Ask a Guy

Are you a good kisser?
Am I your type?
Do you know how good-looking you are?
What do you usually wear to bed?
Do you catch often catch yourself fantasizing about me?
Have you ever thought about us in an intimate setting?
Do you think I’d look good in yoga pants or a sundress?
What should I do to grab your attention?
Can I see your tattoos?
Are you shy in the bedroom?
Can I kiss you?
Do you like to big spoon me?
What, according to you, is my best physical asset?
Name some of your wildest kinks.
How do you see me now?
Are you a lights on or off person?
Narrate me a story from one of your most erotic experiences.
Do you like the idea of ‘Truth or Dare’ in the bedroom?
Did I do a good wax job?
Can you apply some sunscreen on my back?
Are you sure you aren’t a Wi-Fi? because I am feeling a connection here.
I don’t kiss and tell. Do you still trust me?

Questions to Ask a Guy Over Tinder

How’s Tinder treating you so far?
Which shows are you busy binge-watching nowadays?
What is your comfort food?
Would you rather be able to teleport or time travel?
If you are deserted in an Island, then what are the 3 things that you will need.
Are you a movie buff or a bookworm?
Can you tell me more about yourself?
How is your experience with this dating app so far?
Who is your favorite character from the TV show Friends?
What’s the most embarrassing moment that happened to you in high school?
What is a sign of a healthy relationship?
What’s your favorite family memory?
What are your thoughts on ‘Love at first Sight’?
Which quality in a woman do you find most attractive?
Are you an adventurous person?
Do you enjoy being outdoors during your free time?
Which is your favorite go-to restaurant here?
If you could be any fictional character, who would it be and why?
What is the craziest thing that you have witnessed in this app?
Tell me some of your all-time favorite songs.
Has any girl on here used a pickup line on you? If so, then what was it?
Do you enjoy staying up and talking to someone new?
Are you a practical or emotional person?
What genre of movies are you into?
Thoughts on ghosting?
How many hours can you go without using your phone?
Did you come across any disaster dates on Tinder?
Are you on TikTok?
What do you usually have for breakfast?
Do you have any weird food combination that actually goes well?
What do girls usually notice about you from the get-go?
Hit me with your favorite pickup lines.
Have you ever created a fake profile on other dating apps?

How to deliver the best personal question prompt to a guy

Trying to build a connection with someone is challenging. Yes, it is! Although some simple tips can help to increase your chances of getting a positive response.

1. Be confident

Keep your prompt short and sweet. Be confident in your delivery. He’ll see that.

2. Make eye contact

Don’t keep your eyes down to the left or not facing him. Make direct eye contact when asking the question.

3. Be prepared for a response

Fold your hands, listen closely, and let him speak. Listen carefully to the words he’s expressing and use that as your method for continuing the conversation.

FAQs

What are some ways to avoid having a woman respond poorly to questions?

Make sure that the timing is right. Do the both of you have the opportunity to create a discussion? Are you going to be able to listen attentively? Choose the right setting to create success.

What should I avoid asking?

Avoid questions that don’t seem personal. Make sure that you have a good understanding of who they are and what they stand for. Then pick questions that you know will have a good chance of success.

Questions to ask a guy (images to share)

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Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.