50 Great Questions To Ask A Guy

50 Great Questions To Ask A Guy

Got a crush on a guy you know? Maybe he’s a co-worker… or a classmate, or even some guy you met out in the world. Whoever he is – you probably want to know more about him.

So with that in mind, here are some great questions to get to know him:

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1. You get to marry one fictional character – who is it?

2. If you didn’t have to worry about money or a job, where would you live in the world?

3. What was the last book that you got so absorbed in that you couldn’t put it down?

4. In your mind, what are your 3 biggest weaknesses?

5. You only get 3 words to describe yourself – what are they?

6. Which is better to listen to – your heart or your brain?

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7. Do you consider yourself a spiritual person? How about religious?

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

8. What kind of extra-curricular activities did you do for fun in high school?

9. What’s your weirdest pet-peeve?

10. Which is better: asking for permission or asking for forgiveness?

11. What would you do if you inherited 1 million dollars tomorrow?

12. What’s the most embarrassing moment of your life so far?

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13. What fictional character do you identify with the most?

14. Are you a superstitious type of person? About what?

15. Where would you rather live – a big house in the suburbs or a tiny apartment in a great location in the city?

16. If you could have any job in the world, what would it be?

17. Ever have any trouble with the law or get arrested?

18.Which do you like more, a great book or a great movie?

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19. Do you think it’s important to keep up with the news or do you not care?

20. What’s the nicest thing you’ve ever heard about yourself? What do you want to hear about yourself?

21. What do you want to have going on in your life in 5 years, or 10, or 15?

22.Which would you rather be, smart or happy, and why?

23. You can have one superpower – and only one. What is it, and why did you pick it?

24. What’s your biggest regret that you have in your life so far?

25. Which show on TV do you absolutely have to watch live when it airs?

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Ask Him These Top 25 Funny Questions To Get Him Laughing

1. When did you have your first kiss and who was it with?

2. If you were a waiter and a customer was a jerk , would you spit in their food?

3. What’s your favorite food to eat?

4. What’s your favorite type of music to listen to?

5. What’s the one movie you love more than any other movie?

6. If you could only eat one food for the rest of your life, what would it be?

7. What’s the funniest thing that’s ever happened to you?

8. Has anyone ever walked in on you naked?

9.How do you deal with people in your life that you don’t like?

10. What’s the funniest thing that happened in your childhood?

11. Do you like waking up early or staying up late?

12. What are you most afraid of?

13. What actor would play you in a movie about your life?

14. Guess – what am I thinking about right now?

15. If you had to give me a nickname right now on the spot, what would it be?

16. Do you think it’s possible that we met in a previous life?

17. Pick one to live in: beach, city, or country?

18. How would you describe me to someone who doesn’t know me?

19. Which describes your personality… naughty or nice?

20.What’s the sexiest animal in the animal kingdom?

21. Who’s a celebrity you have a crush on?

22. You get to date one famous celebrity – who is it?

23. If you had the power to read someone’s mind, whose would it be?

24. What would you do in a week if you were told you only had a week to live?

25. Did you ever cheat on a test in school?

If you loved this article, then check out these other must-see related posts:

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How to Talk to a Guy and Make Him Like You

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

Take The Quiz: Does He Like You?

114 comments… add one
  • Fa Yo Kemi March 10, 2021, 1:54 pm

    I think dis is gonna work for him
    But I also need to know how to make him want for more
    I mean more of our chat

  • Anderson.Julia April 29, 2020, 9:24 am

    A person’s success does not depend on his wisdom, but perseverance

  • sue May 31, 2018, 10:04 am

    I think you should do this more often
    I love reading these every single day
    keep up with it
    thanks for putting it out for every one
    to see!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

  • sue May 31, 2018, 10:00 am

    I love this questions I am a big fun

  • cynthia lee arthur February 21, 2018, 3:40 pm

    john, would you like to go out for a drink?

  • help me December 29, 2017, 3:48 am

    Hey I need help.I just broke uo with someone and now I like this other guy who is now my bf but he always seeking attention and it get annoying. I dont wanna break up with him other wise I would have dated 2 guys in less then 6 months and that is kinda gross and slutty. So what should I do.

    • Helper September 3, 2018, 7:20 pm

      you shouldn’t worry so much about what other people would think because let’s be serious, its okay to date in less than six months, it just means that there are certain circumstances that causes problems with the relationships that can lead to break up. Break up with him if he isn’t the one don’t put yourself through that torture.

  • Lily December 11, 2017, 11:52 pm

    Lol I found those amusing. My bf and I can talk about literally anything… so it was fun asking him some of these questions

  • Big Shaq December 8, 2017, 4:17 pm

    The ting goes skraa pop pop pop pop pop skraa du pop pop and the ting goes poom poom skyaaaa pom pom pin pom pom pom, ya u dunno big Shaq

  • Fillintheblank December 6, 2017, 9:48 pm

    answer these questions first :)
    1. who is your bestfriend?
    2. how many boyfriends/ girlfriends have you had?
    3. describe me
    4. would you help me if i have a trouble?
    5. who is your crush?
    6. make the same post to your instagram story

  • hmvo September 1, 2017, 6:01 pm

    All in all though, it s a great question to ask to find out some of the things he s done and the things that he thinks are important.

  • oras4ios.com August 29, 2017, 1:43 pm

    What really makes this question fun is imagining what the celebrity would do once they were leader and what kinds of laws they would make.

  • Charity August 1, 2017, 10:37 am

    These are really good questions!!

  • Jaelie July 23, 2017, 10:54 pm

    I’m 13 and I like this guy he’s 15 and we have a lot in common and we kinda flirt but I don’t know if he likes me….what do I do?

    • kelvin July 25, 2017, 11:47 am

      its awkward for a girl to be the first to approach a guy with her intention otherwise he’ll take you for granted along the line (depends) – cos he is still young and may not know the value of a girl approach for now, but when he is in his 30’s he will. However, Jaelie wait for him to say something. If he is a shy guy help him out by given him some hints like asking him if he’s up for a walk down your street in public day time, this might also help cos a lot can be talked about and he shouldn’t be shy walking beside you in public… Lastly during a conversation, ask him if he has a girlfriend-now the answer is in two path YES/NO which brings more questions.. You hope he says No – then ask him if there is someone he like’s but haven’t got the COURAGE to tell? his answer should also help you know your next step!! But remember, be careful being the first to say your feelings to a man! 80% will take your feelings for granted – men like to fight for what they believe in… but remember your friend is 15.. so do not overate him as a man, he is still in his learning stage as yourself as 13.. take it slow but i’ll advise you to talk to your mom about him, your parent are best in helping you out make the right decision pertaining a boy! stay blessed Jaelie..

  • Rachele May 19, 2017, 12:19 pm

    This general list is definitely a start to getting to know another person that you may be interested in. I believe that if our person of interest finds these interesting to answer and are capable of answering them, they certainly may be a great candidate to consider spending your time with.

  • abby May 4, 2017, 10:16 am

    i have that same problem but dont push him he will come around

  • Arieyanah Ross April 1, 2017, 7:33 pm

    these questions are shady

  • Leisha March 20, 2017, 12:35 pm

    These… Questions… Didn’t… Help…

    • Danielle George September 12, 2017, 9:52 pm

      Thank you…. at least i’m not the only that thinks that

  • Yah yah March 9, 2017, 11:36 pm

    Hi umm so I never had a bf but I’ve done things but I got a bf so now it’s weird cuz the guys I was talking to before keep talking to me wanting me but I wanna stay Loyal

    • Star May 17, 2017, 9:14 pm

      Stay true no matter what

  • Mia Vickerman February 28, 2017, 11:50 am

    I want to know how to get him to like me i tried looking it up online and i never get any research that good enough…. Hopefully someone can help me.. Cause i really like this guy he makes me smile like nobody in the whole world could hes soo cute and very nice i want him to feel the same about me…. Can you help me??

    • Selena May 15, 2017, 1:11 pm

      If u really want him in your life Jst say it to him plz don’t search in internet express your feelings to him I am sure he will understand you

  • Kawsar ahmed February 25, 2017, 12:25 am


  • Sadia shoukat February 13, 2017, 4:16 am

    Its a very amazing. And i like this page

  • Divya January 22, 2017, 10:33 am

    Just get more closer to him… Day by day… Do something in common… Go to the park with him… Speak more with him… When he is worried console him… Never confess your love to him… It may even break your friendship… Without even saying a word try to communicate more with your body language… After some time he will realise your love… Then make a situation for him to confess his love for you…

  • Arabella Kriedeman January 5, 2017, 10:29 pm

    Hello ilovecandy, so maybe you should tell him. Just to get it out there. If a ton of people are into him than it may not be a difference. But if not many girls are into him than it may be impactful and he will start to like you… idk

  • peace daniel November 24, 2016, 4:54 pm

    if a guy likes u and a new girl comes will he still like u or he will like the new girl, he doesn’t talk to me but he talks to my friends does he like me?

    • Wastelxndsx January 16, 2017, 10:43 pm

      It all depends on how he acts around you… if hes into you he’ll either flirt by messing with you or will flirt like anyone else.

  • Bob November 18, 2016, 9:14 pm


  • Australian girl November 16, 2016, 7:17 pm

    What happens if your 13 and he’s 15 and your going out on your 1st date with this guy what will he think of if you ask him what does he think his super power will be if he gets them?

  • Yama August 15, 2016, 9:12 am

    Hi guys all idea is good

  • Zara July 28, 2016, 8:12 am

    Great ideas. I asked these with my crush and we nowliterally know everything about eachother. Thank youuuuuu !!! We r now going out !! Yayyy x

    • Yama August 15, 2016, 9:33 am

      Ya ur right

  • kflwF?LN June 2, 2016, 10:41 pm


  • Lydia May 30, 2016, 11:59 pm

    i did and it went really well

  • A guy April 16, 2016, 1:18 am

    Dont ask these questions
    For real dont

    • Ershaille November 12, 2016, 1:34 pm

      Lol true!! don’t!!

  • Karen Sutton January 18, 2016, 2:47 pm

    In a situation like a first date, how many of these should you go with?

  • Vivian Irvin January 15, 2016, 8:26 pm

    Most of the men that I meet do not care about learning more about me.

    • Shante maxwell June 28, 2016, 10:39 am

      That’s not good. If a man has no interest in getting to know you as a person. Then he doesn’t want to know you? Push past his ass girl!

  • Michele Lasalle January 14, 2016, 9:06 pm

    I like how you have them broken down into two categories. I don’t think that makes any difference and you can ask any of them any of the time.

  • Tammy Arney January 13, 2016, 11:22 am

    I would generally like to have a guy that keeps up with the news to a degree. It gives you more to talk about.

    • Donna Gass January 18, 2016, 2:56 pm

      I like current events too, so that would be a good thing to have in common.

  • Elfriede Hill January 12, 2016, 5:58 pm

    I have been around guys that the real defensive over stuff like this. Why would they?

  • Phylis Quach January 12, 2016, 5:50 pm

    I love every one of these. I was picturing what answers I would be getting if I asked my husband these.

    • Mindi Scott January 14, 2016, 9:17 pm

      This post could turn into a real fun Saturday night at our house. There are a lot of fun questions you can ask just about anyone.

  • Gladys Frye January 11, 2016, 9:42 pm

    The superhero question is a good one. It really lets you into the type of mind they have, about themselves.

  • Mary Gee January 8, 2016, 1:28 pm

    Asking how they feel about current events is a good question in my opinion. Some people do not like the news, but also seem out of touch in some ways.

  • Frances Griffin January 7, 2016, 10:38 pm

    I do not see any reason why you wouldn’t want to try out some of these questions to get to know someone.

  • Maria Carroll January 6, 2016, 2:54 pm

    When it comes to getting to know a guy, these are very good questions to ask. Then you just have to hope he’ll open up about them.

    • Deborah Lininger January 8, 2016, 1:35 pm

      Yeah, these types of questions will really give you a chance to dig into the type of person he is.

  • Sharon Miller January 5, 2016, 9:59 pm

    You really want to see a guy freak out, ask him is he has a 5-year plan!

  • Sharon Williams January 4, 2016, 9:39 pm

    This is very true.

  • Susie Alexander January 4, 2016, 9:30 pm

    I always wonder what others are saying about me, good or bad. I really have never heard anyone say anything nice within earshot and would feel weird asking others about it.

    • Shala Gruber January 7, 2016, 10:27 pm

      I thought I would want to know what others are saying, but I am glad that I passed that stage of my life up. You just never know what you are going to get.

  • Carole Wiley January 1, 2016, 10:10 am

    I wonder what my husband would say if I asked him about marrying a fictional character.

    • Bertha Finch January 5, 2016, 10:09 pm

      Do you really want to know? Some people might take it too personally and that could ruin a good thing.

  • Esther Lankford December 31, 2015, 8:48 am

    I use some of these on dates and then I make up my own to really drill into what type of person I have before me.

  • Diane Franklin December 30, 2015, 9:33 am

    These are all great questions. They would go the same for a guy meeting a girl for the first time, that is the best part.

    • Ursula Kelly January 1, 2016, 10:24 am

      yes they would. I have used them both ways and just about anytime that I meet someone new. They are great icebreakers.

  • Eleanor Washington December 29, 2015, 8:37 am

    I like to use questions like this to feel a person out. You can learn a lot from them because the questions are pointed to get information you wouldn’t normally get in normal conversation.

    • Rachelle Wade January 6, 2016, 3:22 pm

      Me too, it is a great way to break the ice, like others have mentioned. You can also have a real fun time with the answers too.

  • Lucy Noda December 28, 2015, 1:20 pm

    Some of these are like playing a game of “Would you rather?”

    • Consuelo Frazier December 30, 2015, 9:42 am

      Totally. But it allows you to get a good bit of information about the person.

  • Rachel Engler December 28, 2015, 1:05 pm

    IF you are looking for a first date question resource for men, there isn’t any other better on than this post!

  • Brittany Snowden December 27, 2015, 9:26 am

    I have asked guys to describe themselves in 3 words and that is a great way to really see what they think of themselves.

  • Willie Suarez December 26, 2015, 12:15 pm

    I was always told that it was easier to ask for forgiveness later than it would be to ask for permission now. OF course, my father was the one that said it :)

    • Karen Putnam December 29, 2015, 8:46 am

      I agree with that in some cases.

    • Angelia Casarez January 15, 2016, 8:37 pm

      I heard that somewhere also. I think my boss told me that one time.

  • Jennifer Eastman December 24, 2015, 12:21 pm

    I am going to use some of these as ice breakers the next time I go speed dating :)

    • Cynthia Schaff January 13, 2016, 11:44 am

      That is exactly what they are used for!

  • Jessica Portillo December 23, 2015, 10:00 am

    Great ice breakers for a first date.

    • Judy Berg December 27, 2015, 9:39 am

      That is what I was thinking. I am going to have to make notes from this list.

  • Vickie Harrington December 23, 2015, 9:50 am

    its weird about the superpower, the guys get so arrogant about it LOL.

  • Kathy Lewis December 22, 2015, 12:45 pm

    I like to ask about embarrassing moments because it will really show you if the guy is going to open up to you or not.

  • Linda Shay August 25, 2015, 9:39 am

    I know what I would answer to “what food I would eat the rest of my life”.

    • Mickey Brown December 22, 2015, 12:57 pm

      This is a good one. You will know what food they are so passionate about they would spend the rest of their life eating it :)

  • Judith Mitchum August 25, 2015, 9:29 am

    I do not think i would ask about the biggest regret. You never know what the answer might be, plus he might clam up because it is something he does not want to talk about.

  • Tami Newton August 24, 2015, 9:04 am

    What a great list of questions. The problem I usually have is when some of these questions are asked of me ;)

    • Rochelle Frazier December 26, 2015, 12:31 pm

      Yeah, if you want to see some sort of bumbling idiot, then you are going to have to ask me some of these!

  • Rochelle Marshall August 22, 2015, 6:12 am

    I used to just fly by the seat of my pants during the first couple of dates, but that has not been working too well for me. So, I am going to take this list down and repeat some of them so I can remember them for next time!

    • Janet Green December 31, 2015, 8:57 am

      That sounds like a real good idea!

  • Eva Douglas August 22, 2015, 6:03 am

    Great questions. Perfect icebreakers for the weird silence during a date.

    • Leticia Kidd December 24, 2015, 12:31 pm

      Yes they are. I have used many of these and they really can get the conversation going.

  • Christina Evans August 20, 2015, 9:39 pm

    Smart or happy and why? That is a great question to ask. I am going to have to remember that one!

  • Judy Moore August 19, 2015, 8:53 am

    I think the question, “Did you ever cheat on a test in school”, would get you a funny reply. Most guys that are asked these types of questions might deny them, but the ones that speak up and answer, are a better person to be with anyways.

  • Melanie Snyder August 19, 2015, 8:38 am

    I wish I could hear nice things about myself. The sad thing is that most praise is not mentioned right to the person and behind their back instead.

    • Carole Norman August 20, 2015, 9:48 pm

      I am sure that people are saying nice things about you. Even if you are not hearing them, they are there!

  • Lynn Webster August 18, 2015, 4:48 pm

    If there is a guy out there that can describe himself with three words that YOU want to hear, he is totally a keeper. That would be a good test for a date later on down the road.

    • Annie Ellington January 11, 2016, 9:51 pm

      Oh yea, but usually there is a word or two that make it into the description that turn you away quickly.

  • Jaquelyn Elder August 17, 2015, 9:10 am

    I think asking, “how would you describe me to someone that does not know me” is a great question. The problem is that he is answering it to YOU and that might skew his reply.

  • Joy West August 14, 2015, 11:48 am

    Well, isn’t this a nice list. Usually I am the bumbling idiot at the table, but it looks like I can at least get some direction by asking these questions!

  • Lisa Bennett August 13, 2015, 5:45 pm

    This is a great list. It gives people a great starting point when first meeting.

  • Phyllis Hoffman August 13, 2015, 4:38 pm

    LOL. I like this. Very good way to start a conversation with a new crush!

    • Kristy Moreno August 24, 2015, 9:13 am

      yeah, i needed a list like this just to make sure i have something to say on a date!

  • Alice Lewis August 12, 2015, 9:49 am

    I used to think that I would never need to prepare for a date with something like this, but after a few weird silent moments recently, I am starting to think reviewing a list like this might not be a bad idea!

  • Louise Robinson August 12, 2015, 9:37 am

    I like to ask the pet-peeve question right away. That way, I am aware of what not to do to get under his skin. Makes sense, right?

    • Patricia Simmons August 17, 2015, 9:24 am

      I have used this as my go-to question, but it has backfired on me more than one time. The guy would normally reply with the answer, but once in a while, there is a guy or two that will get defensive and weird about it.

  • Holly Gill August 11, 2015, 9:29 am

    Ohhh, I have a crush on a guy that works at Starbucks and I have been going there every day because of it :) I am going to toss a few of these at him when I get the chance to see what his reaction might be.

  • Marcella Greer August 11, 2015, 9:19 am

    I have been told that my sense of humor is why guys like me, so that second list of questions is perfect for me!

  • Sharon Morris August 10, 2015, 7:24 pm

    These all seem like good first date questions. If I have been with someone for a year or more, I would expect to know all the answers to these.

  • Kayce Arnold   August 7, 2015, 9:24 pm

    Getting in trouble with the law is a great question, but it might be one that is better not asked right away.

    • Harriet Fernandez August 14, 2015, 12:07 pm

      You got that right. This is a great list of “icebreakers”.

      • Susan Kelly August 18, 2015, 4:59 pm

        I always have a hard time getting the conversation going with a guy. Do you really think these would help me with that problem?

  • Novella   August 7, 2015, 8:25 am

    Thank you for posting this list. It will give me something to think about for my date coming up!

    • Hannah Peters August 10, 2015, 7:35 pm

      I agree, great date questions. I would like to take this list to a speed dating event LOL.

  • Sadie   August 7, 2015, 8:10 am

    Oh man i love the “three words to describe” question. It usually starts an interesting conversation.

    • Anne Metcalfe August 7, 2015, 9:36 pm

      me too, you just never know what you are going to get. the bad thing is if he asks you the same thing back :)

  • Novella   August 6, 2015, 9:35 pm

    Do you know what it would take for my b/f to even sit long enough to answer any of these? He is so sad. Maybe if I asked the questions through a video game he might pay attention.

  • Sadie   August 6, 2015, 9:23 pm

    I like to ask the “what job if any in the world” type questions because it is usually something they are not doing and can get a good conversation started that is clean.

  • Lavonda Streets   August 5, 2015, 12:10 pm

    Laughter is a great way to calm the both of you down during an awkward date. I like this list, it gives me great ideas for the next time. I just have to make sure that I am not going to talk the entire time :)

  • Jade Weatherford   August 5, 2015, 11:57 am

    This is a real good list for those that are going on a first date. Sometimes, usually happens to me, there is a weird silence and these are good ice breakers!

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