352 Questions to Ask a Guy

352 Questions to Ask a Guy

This article will change the way you talk to men. It will assist you in becoming great at having conversations, and eventually becoming totally comfortable with any guy you happen to be around.

All men are different, and certain men will obviously enjoy different questions more, but this article is going to give you options to choose from, as well as help select exactly what you need for your specific situation.

These questions work well on just about any guy; “intimidating” men, successful men, shy guys, guys who typically don’t open-up, creative guys, older men, serious ones, laid back guys, younger men, quiet ones – virtually any type of man you can think of! With these questions you’ll be covered!

These questions are your complete guide to give you the ability to have an effortless conversation and connection with any guy you want.

But before getting to the list, I’m going to share a secret with you: men want to open-up! The issue is most women don’t have a clue about this, and moreover, don’t know how to correctly make a man feel comfortable enough to speak his true feelings. The funny thing is, if you do it correctly, most men will enjoy talking about deeper subjects, and at the very least it can be cathartic.

Believe it or not, men, just like anyone else, love talking and get excited by that feeling when you realize you can be fully candid with another person. Especially if that person is a woman!

Being “that woman” who gets him talking will literally be what separates you from all the others.

Emotional connections are very addictive, and with each answer your bond can only grow.

What I truly believe to be imperative to a constructive conversation is not responding with judgement. Always have an open mind and let the conversation flow naturally. Any sign that what’s being said to you is being looked down upon will make a guy clam right up.

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

Being judgmental or discerning is the worst thing you can do.

With these questions, they’ll be no more moments wondering of what to say, being embarrassed, afraid of rejection, or even making a fool of yourself. If you read to the very end of this article, I can promise you, you will be able to have any kind of conversation with any type of man and most importantly, feel good about it! It will help you end any feelings of confusion and to establish a closer connection with any man.

These are the creme de la creme of questions! They are specifically designed to achieve a purpose. I’ll explain the general purpose of a few with some examples first, and then give you the lion’s share with strictly questions after.

Heartfelt Questions

Take note, the purpose of this kind of question is to capture his vulnerability; his heart behind the mask he wears to society. But warning, men don’t really enjoy this kind of question; so, ask sparingly and only when the time comes up organically.

Forcing this kind of question will end up being very awkward, so don’t do it in a way that feels pressured.

So, if you do ask something heartfelt, start small. Men generally will not share intimate information unless they start to or do feel a true authentic connection. This is how you reach his heart. Here are a couple of examples.

  • What song makes you cry?
  • Who or what do you love more than anything in the world?
  • What do you remember most from your childhood?
  • Anything special in particular?
  • What’s the sweetest thing you’ve done for someone?

Nonjudgmental Question

It is important to show you do not judge, so he answers your questions honestly. This opens the gateway to truly honest conversation.

  • Do you have any insane turn ons?
  • Ever been to jail?
  • Ever been in a cop car?
  • What is the craziest thing you have done?
  • Is there anything you have done but would never tell anyone?
  • Deepest, darkest secret?
  • What do you feel most ashamed about from your past?
  • If you could murder someone would you?
  • What is your biggest regret?
  • Biggest lie you ever told?

You should always preface this kind of question with something to ease the tension. Something to the effect of, “I hope you know I would never judge you… I know who you are, and nothing will change that…etc.”

As I’ve said, and I’ll say it again, men need a safe, nonjudgmental zone to open-up to you. This kind of question gives you a way to show him you’re not being critical.

A Funny Question

This opens the door for him to share a funny experience with you. It’ll show you his sense of humor. Connecting on this level is key! Humor is definitely a great way into a man’s heart, and you can also learn a lot about someone by what they find funny. For instance:

  • How much would you have to get paid to sleep with (insert name of choice here)?
  • Most embarrassing moment of your life?
  • Favorite comedian?
  • Stupidest thing you’ve ever done?
  • Funniest thing you’ve ever gotten away with?

If you need more, I’ve got a great article about humor and relationships here:

Funny Questions to Ask A Guy

Caring Questions

The purpose of these questions is to understand what he perceives to be kind. You are obviously not heartless, but much too often men perceive women to be much less caring than they are.

When you discover what he perceives to be caring behavior, you can internalize this and begin to build a caring dynamic within your relationship.

  • Would you take care of me if I was sick?
  • How do you normally deal with stress?
  • What do you find the most comforting?
  • Does being babied annoy you?
  • What is the sweetest thing anyone has ever done for you?

These are just some examples with some reasoning and explanation to give you an idea of how you can learn by asking questions, also why and when to ask them. Now, I will give you the following categories, so you can know what to ask in any situation!

Icebreaker Questions to Ask A Guy

  • Where are you from?
  • If from somewhere different than you, what was your favorite and least favorite part about growing up there?
  • Do you have any siblings?
  • What does/ did your father and mother do for work?
  • Do you have any wacky family members?
  • What’s your dream job?
  • Do you enjoy your job right now?
  • Where do you see yourself in 5 years?
  • So, have you ever had any “crazy” ex-girlfriends or odd relationship experiences?
  • What’s your favorite type of music?
  • What’s your favorite hobby?
  • Do you enjoy working out?

MORE: 20 Questions to Ask a Guy You Like to Get Closer

Naughty Questions to Ask A Guy

  • So, are you single? Just curious…
  • So… wait, you’re single? How does that happen?!?!
  • Have you ever had anyone say you look like… (insert actor they happen to look like here)
  • Has anyone told you how handsome you are?
  • Do you have any “odd” turn ons?
  • What’s your weirdest date experience ever?
  • What’s one thing that you’ve always wanted to try but never gotten around to doing?
  • What’s your favorite sexy film and why?
  • Biggest turn off?
  • What was your first kiss like?
  • Biggest turn on?
  • Are you turned on if a woman is in control?
  • Are you ticklish?
  • What would you do if I tickled you?
  • How often do you enjoy having sex? (A.K.A. every day or every week?)
  • Do you think it’s hot to have sex in public?

MORE: 52 “Naughty” Questions That’ll Turn You BOTH On

Questions to Ask Your Crush

  • If you could stop on horrible thing that is happening in the world right now what would that be?
  • What’s one superpower you wish you had?
  • If you were invisible for a day what would you do?
  • Would you rather be known in life and forgotten, or unknown in life and remembered forever in death?
  • What’s one trait you look for in a best friend?
  • Is there anything you want to accomplish before you die?
  • If you had to spend a million dollars in a day what would you spend it on?
  • If you could only have one drink for the rest of your life what would it be?
  • What’s your favorite weekend activity?
  • Do you believe in astrological signs?
  • Do you have any guilty pleasures?
  • If you could be born again and completely repeat your life, would you?
  • What’s your biggest pet peeve?
  • Have you ever yelled at someone?
  • What’s the meanest thing you have ever done?
  • What’s your closest experience with death?
  • Have you ever known someone that has been seriously ill?
  • Is there anything in your life you can’t get over?
  • What’s one thing you’d die without?
  • Could you go a month without technology?
  • What’s the most you have ever eaten?
  • What was the best gift you have ever received?
  • Do you like going out or staying in?
  • What the worst thing someone has done to you?
  • Do you have a favorite song?
  • Who’s your favorite musician?
  • Favorite artist?
  • Do you know what it feels like to have your heart broken?
  • How would you describe the feeling of being in love?
  • What’s the biggest turn off in the world to you?
  • Have you ever done anything ridiculous to get a girl’s attention?

MORE: The Best Questions to Ask Your Crush (And Exactly How To Talk To Him)

Deep Questions to Ask A Guy

  • How long do you think you’ll be remembered?
  • Who do you think would show up at your funeral?
  • What would you have inscribed on your tombstone?
  • Who would receive benefits from your will?
  • What will people say about you in your obituary?
  • Have you ever had a close experience with death?
  • Have you ever had some close to you die?
  • Are you afraid of death?
  • Who would you feel justified in killing?
  • Would you die for a cause?
  • What’s your best childhood memory?
  • What is the most important event that ever happened in your life?
  • Biggest fear?
  • Biggest regret?
  • Happiest you have ever felt?
  • Saddest you have ever felt?
  • Most alone you have ever felt?
  • Do we really have control over our lives?
  • Is it fate or destiny that controls us?
  • Is life fair?
  • Biggest fear that you conquered or had to overcome?
  • Have you ever felt hopeless or like you want to give up in life?
  • Have you ever been in serious trouble with the law?
  • Have you ever struggled with substance abuse?
  • What’s the most embarrassing experience of your life?
  • Do you have any prejudices for certain things or people?
  • Do you hate anything?
  • Do you have any obsessions?
  • What was your first sexual experience?
  • Do you have any phobias?

MORE: The Best Deep Questions To Ask a Guy (Or a Boyfriend Or Man You Like)

Fun Questions to Ask A Guy

  • What’s the most awkward/ cringe worthy thing that has ever happened to you?
  • If you were forced to eat a single cuisine for the rest of your life what would it be?
  • What’s on your “bucket list”?
  • What’s your view on reality tv “stars”?
  • If you had a reality show what would the premise be?
  • What kind of characters would your family be in the show?
  • What is the most ridiculous thing you have ever seen?
  • What’s the dumbest fashion trend going on right now?
  • What would your mom do if you became a gangster rapper?
  • What is the last car model you would choose if you were forced to have a single car for the rest of your life?
  • What’s one thing that makes you just snap?
  • Do you have any pet peeves?
  • Do you have any extracurricular talents?
  • What’s your favorite hobby?
  • If you could move and live anywhere where would that be?
  • If you could cancel one tv show which one would it be?
  • If you became the president what’s the first law you change?
  • What’s the funniest catch phrase you’ve ever heard?
  • What’s the stupidest way you have ever hurt yourself?
  • What’s your favorite movie scene?
  • Do you have a song you just cat help but sing along with?
  • Have you ever gotten away with anything “bad”?
  • If you had an invisibility cloak what’s the first thing you’d do and where would you go?
  • What’s your biggest phobia?

MORE: Fun Questions To Ask A Guy (Rejection Proof!)

Personal Questions to Ask A Guy

  • What’s your biggest fear in life?
  • What’s your biggest regret?
  • What’s the most important thing that happened to you in your childhood?
  • Have you ever hated someone or something?
  • Do you think one day technology will be so advanced we may live forever?
  • Do you think humans will ever know the real reason behind existence?
  • Do you think be conscious is a blessing or a curse?
  • Do you believe in extraterrestrial life?
  • What do you think finding life other than ours in the universe will do to change our society?
  • In the future could you ever see an Orwellian universe controlled under a new world order being played out?
  • Do you think one day the earth will reach its maximum population causing the destruction of humanity?
  • Would you ever feel justified in killing someone?
  • Have you ever felt so passionately about something you would die for it?
  • Have you ever almost died before?
  • Have you ever had a close family member or a friend pass away?
  • How long do you think you’ll be remembered after your death?
  • Do you believe in life after death?
  • Do you believe good people will be ultimately rewarded for their charity and sacrifices?

MORE: 50 Personal Questions to Ask a Guy (That Really Open Him Up!)

Philosophical Questions to Ask A Guy

  • Do we really have control over our lives?
  • What is the purpose of being happy?
  • Is it fate or destiny that controls us?
  • Is being conscious a blessing or a curse?
  • Is life fair?
  • Thomas Jefferson once said “the art of life is the art of avoiding pain”- do you agree with him?
  • Is there a difference between living life and just existing?
  • Does everyone have a unique purpose on this earth?
  • Do you like to celebrate the good parts of your life in any special way?
  • We all feel we are “meant” to do something, that we are “here for a reason” and have purpose- is this true, or is it an inherent genetic delusion to keep us motivated and positive?
  • What’s one experience you’ve had that totally changed your view of the world?
  • Does it disturb you that one day in the future, after you die, someone will be the last person to ever think about you?
  • What do you think the point of fear is in human nature?
  • How powerful do you think incentive is in changing humanity?
  • If you could time travel to any era to make your life better what time-period would that be?
  • With the knowledge of the size of the universe that we can prove, and a population of almost 8 billion, how valuable is human life on an empirical scale?

MORE: Philosophical Questions to Deepen Your Relationship

Interesting Questions to Ask A Guy

  • If you could live life as successful criminal and never get arrested, would you?
  • Have you ever been in any insane situations?
  • Have you ever had any “physical altercations?”
  • What’s one thing you would change about the human race?
  • If you could prevent any previous historical disaster which would it be?
  • If you were drafted into the army during a hypothetical war how do you think you would handle combat?
  • Has anyone ever back stabbed you before?
  • Have you ever lost friends, or ended any friendships?
  • If you starred in a reality show what would be the premise?
  • Have you ever been obsessed with anything?
  • If you could invent anything what would it be?
  • If you had to choose a career path for your children what would it be?
  • Do you know how to do anything extremely difficult?
  • What was the easiest class for you throughout your education?
  • Do you think extraterrestrial life exists outside our universe?
  • Do you believe in a higher power?

MORE: 150 Interesting Questions To Ask A Guy Or Boyfriend

Deep Questions to Ask Your Boyfriend

  • Happiest moment in your life?
  • Do you believe in “soul mates?”
  • Do you think one day technology will be so advanced we may live forever?
  • Do you think humans will ever know the real reason behind existence?
  • Do you think be conscious is a blessing or a curse?
  • Do you believe in extraterrestrial life?
  • What do you think finding life other than ours in the universe will do to change our society?
  • What do you think about religion?
  • What would you consider your personal politics?
  • Do you believe in the afterlife?
  • What do you fear most?
  • In the future could you ever see an Orwellian universe controlled under a new world order being played out?
  • Do you think one day the earth will reach its maximum population causing the destruction of humanity?
  • Do you take anything for granted?
  • If you created a miracle cure would you sell it and become a billionaire or give to people for free?
  • How many times have you felt so hopeless you wanted to give up on life?
  • Have you ever had any serious trouble with the law?
  • Have you or anyone you’ve known struggled with an addiction to substance?
  • What’s your biggest fear in life?
  • What’s your biggest regret?
  • What’s the most important thing that happened to you in your childhood?
  • Have you ever hated someone or something?
  • Would you ever feel justified in killing someone?
  • Have you ever felt so passionately about something you would die for it?
  • Have you ever almost died before?
  • What is your biggest turn on?
  • What was your first sexual experience like?
  • What’s the worst thing you’ve ever done to someone?
  • Have you ever had a close family member or a friend pass away?
  • How long do you think you’ll be remembered after your death?
  • Do you believe in life after death?
  • Do you believe good people will be ultimately rewarded for their charity and sacrifices?
  • Do you believe in any sort of god?
  • Are you religious?
  • In what ways do you measure the value of your life?
  • Do you think that some life has more value than others?
  • What is your final goal in life?
  • What do you think the point of life is?
  • How important do you think our lives are when we know we are such a miniscule component of the entire known universe?
  • If you had one day left to live what would you do?
  • Have you ever felt totally alone?
  • What’s the saddest moment of your life?
  • Why are some people perfect for each other, and why are some people so toxic for each other?
  • Is poverty something that is innate within society or can it be solved?
  • What is the purpose of pain?
  • What is the most unnerving thing to you going on in the world today?

MORE: Deep Questions To Ask A Guy (To Reach His Heart)

Dirty Questions to Ask Your Boyfriend

  • What’s the dirtiest thing you have ever done?
  • Would you watch porn with me?
  • What do you think about edible underwear?
  • What’s the most amazing thing a girl can do to you in bed?
  • Have you ever bought a girl underwear?
  • Have you ever experienced some afternoon delight?
  • Can I watch you get touch yourself?
  • What’s the longest you’ve ever lasted?
  • Do all girls really feel the same?
  • How many women do you think you could have in one day?
  • Do you think being tied up is weird?
  • How far would you go if we played strip poker?
  • bdsm?
  • Have you ever gotten laid in a hot tub or pool?
  • What do you think about when going solo?
  • What is the hottest thing about the opposite sex to you?
  • Do you like watching me play with myself?
  • Who is your favorite porn star?
  • Have you ever recorded anything before?
  • Would you record something with me?
  • Do you like it when girls are waxed or natural?
  • Do you like it when girls wear lingerie?
  • Do you like to be dominant or passive?
  • Are you more rough or passionate?
  • What’s the sexiest thing a girl has done to you?
  • Do you think it’s possible to have a friend with benefits?
  • Have you ever gotten with someone you weren’t allowed to?
  • Do you like getting lap dances?
  • What’s the most insane thing you’ve ever been caught doing?
  • How long do you think you could go with sex?
  • Do you like wearing boxers or briefs?
  • What’s your view on “50 Shades”?’
  • Have you ever had sex more than once in a day?
  • What’s your craziest fetish?
  • What are you thinking about right now?
  • Do you ever get super turned on and forget what you were just thinking about?
  • Last time you had a wet dream?
  • Weirdest sexual fantasy you have?
  • Favorite place to kiss a woman?

MORE: 55 Dirty Questions To Ask a Guy That Turn Him And Make Him Crave Sex!

Cute Questions to Ask Your Boyfriend

  • Who is your least favorite celebrity and why?
  • Have you ever had a celebrity crush?
  • Why do you like me?
  • Have you ever missed me?
  • Would you ever go to space if you had the opportunity?
  • Would you move away with me?
  • If you could live in the universe of any book or movie what would it be?
  • Have you ever witnessed anything paranormal?
  • Who is the last person in the world you would want to be stranded on an island with?
  • What would be your dream vacation with me?
  • If you met an alien what would you do?
  • If you could drive any car what car would that be?
  • What’s your favorite moment with me?
  • If you had to watch one movie for the rest of your life what movie would that be?
  • Do you believe in love at first sight?
  • What’s the most embarrassing thing that has happened to you?
  • What the most trouble you’ve ever been in with your parents?
  • Have you ever had any ridiculous fantasies about a relationship?
  • Have you ever seen anything super cringe-worthy?
  • What’s the cringiest thing we could do in public?
  • What’s one thing that’s makes you burst out laughing?
  • What’s your favorite type of animal?
  • What animal would you describe me as?
  • If you could be any animal what would you be?
  • What is the definition of a soulmate to you?
  • If you could have any superpower what would that be?
  • Do you have any weird family members?
  • What’s the funniest movie you’ve ever seen?
  • Who is your favorite character from a tv show?
  • Do I resemble a character from any tv show or movie?
  • Is there anything you find funny that you used to keep secret?
  • What was your favorite cartoon to watch as a kid?
  • Did you ever fail any subjects?
  • If you could be a billionaire what would you buy?
  • What’s the first thing you noticed about me?
  • What kind of kid were you in school?
  • Do you remember when we met?
  • What’s one thing about me you absolutely love?
  • Do you like giving nice big hugs?
  • What’s your view on pda?
  • Do you think it’s cute to kiss a girl on her forehead?
  • When did you first hold someone’s hand?
  • Have you ever written a poem or song for a girl?
  • Is there anything a girl can do that will make you automatically fall in love with her?
  • How many times have you dreamt about me?
  • How do you cheer someone up?
  • What’s the scariest movie you’ve ever seen?
  • Would you protect me if something happened?
  • Do you like buying me things?
  • Have you ever fallen asleep outside under the stars?
  • If you saw a shooting star what would your wish be?
  • If you could end one evil in this world what would that be?

MORE: Ask A Guy You Like These 20 Cute, Amazing Questions

Existential Questions to Ask A Guy

  • Do you believe in life after death?
  • Do you think suicide is immoral?
  • What do you feel about the death penalty?
  • Is punishing murder with murder hypocritical?
  • Do you believe life has a purpose?
  • Do you think the “Matrix” is real?
  • Do you believe in reincarnation?
  • Does evil exist?
  • Does true pure goodness exist?
  • Do you believe in spirits?
  • Are you spiritual?
  • Do you think you reap what you sow in life?
  • Does what goes around really come around?
  • Is religion an opiate for the masses or is it grounded in some kind of realistic factual situation?
  • Do you consider yourself religious?
  • If you died tomorrow would you change anything?
  • If you had a hour to live what would you say?
  • If you had 24 hours left alive who would you spend it with?
  • Do you think love is real?
  • What is love?
  • Is death final or do we go somewhere when we die?
  • How often do you think about death?
  • Have you ever truly wanted to die?
  • After you afraid of death?
  • Do you think life is happy or is it meaningless?
  • Are we ants and sheep or is humanity special?
  • Do you think aliens exist?

MORE: Deep Questions to Ask a Guy

So, there you go! There is a good question here for just about any predicament you might find yourself in with a guy! Just remember, let the conversation flow and one question will turn into one great conversation!

This article gives you many questions to open up conversations, now in any relationship I’ve found there are 2 pivotal moments that determine if your relationship ends in heartbreak or you get to live happily ever after so it’s vitally important that you take the next step and read this right now, because at some point the man you want is going to ask himself: Is this the woman I should commit to for the long term? That answer determines everything… Do you know how men determine if a woman is girlfriend material (the type of woman he commits himself to) or if he sees you as just a fling? If not you need to read this next: The #1 Thing Men Desire In A Woman…

The second problem almost all women experience: At some point he starts to lose interest. He doesn’t call you back or he becomes emotionally closed off. He seems like he’s losing interest or pulling away – do you know what to do? If not you’re putting your relationship and the future of your love life in great danger, read this now or risk losing him forever: If He’s Pulling Away, Do This…

Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

Take The Quiz: Does He Like You?

33 comments… add one
  • Derry daughty January 31, 2021, 3:01 am

    Thank you

  • dorcus July 19, 2020, 4:05 am

    these questions very good! helped me a lot highly
    recommend these yes

  • Cynthia January 20, 2019, 1:56 pm

    I like this article very much
    Will always follow them
    They really do work

  • demi January 3, 2019, 12:09 pm

    existential questions can be so deep, i wouldn’t ask them on a first or 2nd date. but im open to the topic as long as they interest the guy im seeing.

  • rebekah January 3, 2019, 12:07 pm

    i personally like the interesting questions to ask a guy. i’ve always believed that in any relationship, a good communication is key to making it work. these are really great ideas to keep any conversation going well.

  • calee December 20, 2018, 12:39 pm

    i like reading your posts about how to be better especially in dating and relationships. but i appreciate ideas like these even more because i can just save them and use them in the future. thanks, you’ve been great!

  • amelia December 19, 2018, 12:22 pm

    i like the funny questions. im more into fun and exciting things when it comes to dating. im not really into the all serious crap because it gets boring so fast.

  • amanda December 18, 2018, 12:17 pm

    If i’m really into someone, i would go with the Deep Questions. I like knowing a person’s character thru questions and these are just really great ideas. Thanks for sharing them here.

  • clarence December 17, 2018, 1:06 pm

    i think i like the Interesting Questions to Ask A Guy best. it’s important to really ask these type of questions to get to know someone and to really know if you’re even compatible with each other.

  • abby December 14, 2018, 1:51 pm

    this will be perfect for may date! i met this guy and im just so excited to know more about him. thanks for your help!

  • ashley December 13, 2018, 12:24 pm

    “Dirty Questions to ask you Boyfriend” is my favorite part here. Thanks for sharing your awesome ideas, i will use these to ask my bf for sure!

  • lily December 12, 2018, 4:51 pm

    yes! finally found what i was looking for. i can’t thank you enough for this article! these are really awesome questions!

  • catriona December 11, 2018, 9:04 pm

    i want to know my boyfriend more so i think i should ask him these questions.

  • myrtle December 10, 2018, 12:37 pm

    i love these ideas a lot! thank you for sharing great tips for us to use and take advantage of.

  • stacey December 7, 2018, 12:53 pm

    i’ll go for the dirty questions to ask my boyfriend. i don’t always do this but i think it’s cool to do it every now and then, it would definitely add some spice to the relationship.

  • natasha December 6, 2018, 3:21 pm

    you can never go wrong with these questions! no wonder why a lot of women are loving your site! So many helpful advice!

  • corrie December 5, 2018, 11:26 am

    im definitely saving this link for future reference. im actually going to see a guy i knew from this app. if things go well and we hit it off in person, im trying this list.

  • odele December 4, 2018, 1:46 pm

    really needed this. thank you so much for all of the wonderful dating advice that you give!

  • terri December 3, 2018, 12:47 pm

    these existential questions are what most interests me most. im going to ask them to my date next week. other topics are cool and fun too. thanks for sharing these to us, your readers.

  • kennedy November 30, 2018, 12:29 pm

    these are really cool ideas i can use on my next date. im so excited and i will ask these sample questions esp those existential questions.

  • chantilly November 29, 2018, 12:31 pm

    if i were to ask my boyfriend questions, i would go for the deep and sensible ones. because we’ve been together for a couple of years now, we tend to just do the same things and i realized how much we haven’t been talking. it’s always been work, hanging out and errands in between. these ideas are just great!

  • emily November 28, 2018, 5:22 pm

    great set of questions that i would most likely share with my friends! these will definitely get guys talking even the shy ones!

  • laverne November 27, 2018, 1:18 pm

    definitely dirty questions for my boyfriend! haha!
    thanks for these tips and all others, they will be really helpful.

  • renata November 26, 2018, 1:51 pm

    loving the “Existential Questions” listed here. i will definitely ask these for a new kind of conversation flow with my guy.

  • lexi November 23, 2018, 1:23 pm

    there are so many things you can talk about with a guy. but if you want to have a great conversation, try to ask about things he’s interested in and focus on them esp if these are your common interests. this is the best way to have an easy and fun conversation together.

  • odette November 22, 2018, 6:41 pm

    would you move away with me? – this question is really cute! i wonder what would be my guy’s response if i ask him this.

  • mariette November 21, 2018, 1:15 pm

    i always love having fun and easy conversations specially when im with a guy. these funny questions are really cool, i will use them with a date soon.

  • hailey November 20, 2018, 7:04 pm

    yey! no more questioning of what to say and i can finally say that there will be no more feeling of embarrassment and fear of rejection! will definitely bookmark this page.

  • geena November 19, 2018, 5:46 pm

    wow! these is a huge list and im loving all the ideas you just shared here! thank you for giving us, your readers more reason to get hooked on your website!

  • maegan November 15, 2018, 5:31 pm

    my personal favorite? Existential Questions to Ask A Guy! really interesting topic!

  • arlene November 13, 2018, 4:58 pm

    i want to show my man that i am curious to learn more about him and this random questions are just perfect! thanks for sharing.

  • sofia November 9, 2018, 6:34 pm

    this article is the best! it really changed the way i talk to men! love it! i already shared it with my friends!

  • kallie November 7, 2018, 4:09 pm

    oh i am so excited to ask my boyfriend these amazing questions! your site is really the best! thanks!

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