Random Questions To Ask A Guy

Random Questions To Ask A Guy

These questions will make you come off as spontaneous, playful and fun. Men (for the most part) like women who can go with the flow of conversation, who are curious to learn about them and who get into conversations without being afraid of sounding awkward or weird for asking a question!

Do not worry! Men like being asked questions. Now, don’t get me wrong… do not go crazy and start asking things and persisting if it is uncomfortable for him or an accusatory question; what I mean is..

Men like being asked about things that are genuinely curious and not accusatory in any way. These questions are all curious. So you do not have to worry.

MORE: 50 Great Questions To Ask A Guy

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…

Some questions are stranger than others, some are more playful… regardless, this is a good list to scroll through and pick and choose ones you are particularly fond of.

Random questions to ask a guy:

Are you creative?

Weirdest passion you have?

Do you like math?

Did you like science in school?

Do you have any random special talents?

If you had 3 wishes what would they be?

Do you believe in aliens?

Biggest pet peeve?

MORE: 40 Personal Questions to Ask A Guy

Do you like any comedians?

Have you ever been Catfished?

Do you think social media is ruining our society?

Do you remember your first grade teacher?

Do you remember your first best friend?

Any odd rituals before you sleep?

Do you have a beauty routine? As in, skin care/etc.?

Have you ever eaten so much you fell asleep?

MORE: 40 Personal Questions to Ask A Guy

Worst movie you have ever seen?

Do you take a long time to get ready?

Do you get bored easily?

What is your spirit animal?

Do you like air conditioning or do you get cold easily?

Favorite musician?

Least favorite musician?

Favorite actress?

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

Least favorite actor?

Favorite clothing brand?

Favorite shoe brand?

Do you like any “designer” clothes or do you think wasting money on that is crazy?

Do you believe “luck” exists?

Does fate exist?

Do you ever follow diet trends?

Ever been in a bar fight?

If you could go back to a time period in history which one would it be?

MORE: 215 Questions To Get To Know Someone: Everything You Need To Know!

Do you like Ebay?

Favorite comic book?

Favorite superhero?

Would you ever name your child a name like “Apple?”

Do you like any odd childish games?

How old were you when you first had sex?

Do you like going out with women older than you or younger?

Do you like women who have natural beauty (aka no makeup) or do you like “fake” but hot?

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

Do you like video games?

What is your least favorite movie?

Do you like being alone or do you enjoy company?

If someone went through your room would they find anything odd?

Any interesting conspiracy theories you half believe?

Do you believe in werewolves?

Worst date ever?

What’s your deepest fear?

MORE: 225+ Amazing Questions to Ask a Guy: The Ultimate List

Do you enjoy fighting?

Worst song ever?

Most annoying celebrity?

What would be the worst way to die? Kind of a dark question I know, just curious.

What would you do if you had to run around naked to get $1 million would you do it?

What would you do if you had $50 million?

If you had 24 hours to live what would you do?

Weirdest food you have tried?

MORE: Interesting & Random Questions to Ask a Guy, Girl & Stranger

Favorite food?

Ever had food poisoning?

Do aliens exist?

Ever had the stomach flu?

Favorite food?

Do you think psychiatry over-diagnoses conditions?

What is your dream job?

What is your dream car?

MORE: 50 Good/Funny Questions You Can Ask a Man

Do you think spending a lot of money on a car is silly or smart?

What is your dream vacation?

Do you like going on exotic vacations?

What is the best vacation you have been on?

Do you enjoy cooking?

So you have these questions that will break the ice and make him want to get to know you more, but how do you take your relationship deeper? I want to ask you a question… The #1 Thing Men Desire In A Woman…

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?

22 comments… add one
  • mia May 24, 2018, 2:15 am

    staying in love and attracted with each other is very important in a relationship. there are many ways on how you can rekindle the fire if your relationship suddenly becomes boring and asking your guy some random questions is one of them.

  • katalina May 22, 2018, 5:29 pm

    i always get stuck in a situation where the uneasy silence just stretches on me whenever i talk to a guy. now that i have these random questions, i will surely feel comfortable!

  • louise May 21, 2018, 6:25 pm

    wow! this is a whole list of random and interesting questions that my husband will really enjoy sharing. glad you shared it!

  • phines May 18, 2018, 4:05 pm

    i found what i’ve been looking for in this article! some of the questions in this list are normal, some are weird but i am sure my guy will enjoy answering them!

  • nicole May 17, 2018, 4:42 pm

    i love asking my husband strange and playful questions that he will find entertaining ( becasue nobody wants a boring conversation). this post got everything i need.

  • rhea May 16, 2018, 6:58 pm

    this is the best random question for me – “Do you ENJOY fighting?”– haha! all couples fight but it is not a good thing so he better not enjoy it.

  • gwyneth May 15, 2018, 8:28 pm

    my boyfriend and i will not have a boring conversation anymore! glad i came across these random questions that will make our time together fun as well as interesting.

  • lala May 14, 2018, 4:34 pm

    these random questions will help you know your guy better and not to be used so you can break up with him. you must take the answers casually and don’t be judge mental.

  • emma May 10, 2018, 6:25 pm

    i saw my crush yesterday and would like to talk to him but really don’t know what to say. i want to make a good impression and these random questions can help. i don’t want him to think that i am crazy because of nonsense questions. thanks!

  • gregoria May 9, 2018, 4:29 pm

    questioning will always be a part of a relationship even if you feel that you already know all about your partner. everyday you will definitely discover something new and it can keep you closer.

  • ivee May 9, 2018, 3:03 am

    my boyfriend likes being asked questions and because of that, i can really tell that he is different from other guys. he is very open and not shy to share some personal stuff with me.

  • suzanne May 7, 2018, 10:07 pm

    these random questions are quite nice too. thanks for sharing all your ideas, im sure im not alone in saying they’re really helpful.

  • sienna May 6, 2018, 8:06 pm

    i am slowly learning how to go with the flow when starting a conversation with my guy and i can see that he appreciate me being curious about him. how did i do it? well, i used the random questions in this post!

  • joyce May 4, 2018, 9:10 am

    these are really great ideas! i didn’t think about these before but now i’ll make sure to try these with my crush at the office. hope it works wonders!

  • gloria May 2, 2018, 1:36 pm

    i love this article! a relationship can get boring, so it is very important for couples to have something to talk about. i agree that this is a good list to scroll through if you want to connect more with your guy by asking him random questions.

  • sicily May 1, 2018, 7:16 pm

    i like random stuff and sometimes it’s best to do random things with a special someone. these questions look good to me and i will try them soon. thanks for your ideas.

  • tessie April 30, 2018, 7:11 pm

    not all men are sick of being asked. with the right questions and as long as you don’t sound accusatory, you will surely get straight and honest answers that can bring out sparking conversations.

  • shirley April 27, 2018, 9:54 pm

    having a conversation with a guy can be tough. but with the right questions or topics to talk about will surely allow you to make a great conversation. try these, they’re all very cool!

  • barbie April 26, 2018, 2:56 pm

    these questions are great but i think asking follow up questions will keep the conversation going and make the experience a whole lot of fun and interesting.

  • fiona April 25, 2018, 8:20 pm

    conversations with a guy can make one really nervous at first. try to be as natural as you can be and ask these questions and you’ll soon be comfortable. don’t be too shy to set the tone & pace for your conversation.

  • hazel April 24, 2018, 2:07 pm

    i didn’t know that men liked being asked questions too. i thought it would make them irritable. this post is definitely a big help to me. i can use these random questions to get my guy talking.

  • alexa April 23, 2018, 8:19 pm

    i like these ideas and i can actually use them anytime and anywhere. i met this cute guy and i can see us talking about these stuff to really know each other well.

Leave a Comment