Now when somebody is searching for weird or random questions to ask a guy, well, that may mean many things. These questions lean towards the random and strange. Thus hopefully, that’s what you are searching for when looking for weird and not the 4chan type of weird.
You can flick thru the questions below to see what works for you. As I discussed before, many of those questions are a bit random, and a few are a bit strange. However, all of them are pretty varied. Thus you should be ready to find at least some random questions to ask a guy that may work for the guy you’re asking.
I just like the first and last questions. However, question fourteen is pretty intelligent too. And I’m positive you’ll have one that you’ll like the most. So have a look around and enjoy these weird and random questions to ask a guy.
Here is the list of 100+ Random Questions to Ask a Guy:
25 Random Questions to Ask a Guy
Would you prefer to be smart or happy, and why?
If you could choose one superpower, what would it be and why?
What is your biggest regret in life so far?
If you could marry a fictional character, who would it be and why?
If money and career were no object, wherein the world would you choose to live?
What’s the last book you read that you simply could not put down until you finished?
What television show do you plan your day around in order to see it live?
What extracurricular activities or sports did you participate in when you were in high school?
Of all your pet-peeves, which is the strongest?
Is it better to beg forgiveness or ask permission?
If you inherited or won a million dollars, what would you do with it?
What is the most embarrassing thing that has happened to you?
Which fictional character do you believe is the most like yourself?
Are you superstitious? If so, what are you most superstitious about?
Do you believe it is vital to everyday life to know what is happening in the world around you?
What is the nicest thing anybody has said, or you believe they would say, about you?
What are your life and career goals in 5, 10 and 15 years?
Would you rather live in a large house in the suburbs or a tiny apartment in the city with an excellent view?
What are you three weaknesses?
How would you describe yourself in three words?
Which is more logical to follow—your heart or your head?
Are you spiritual or religious in any way? If so, how?
If you could have any career possible, what would it be?
Have you ever been arrested or contracted any diseases?
Which is better—a novel or a movie?
Funny Random Questions to Ask a Guy
If your life was a movie, which actor would play you?
Would you spit in a customer’s food if you were the waiter and they had been rude to you?
How do you handle people you don’t like?
Is it possible for us to have met previously, in another life?
Where would you prefer to live: beach, city or country?
If you had met me before, how would you describe me?
Do you think of yourself as being naughty or nice?
Who is or was your celebrity crush?
With whom did you have your first kiss?
What is your favorite type of food?
What’s your favorite genre of music?
What is your all-time favorite movie?
If you could eat one meal for the rest of your life, what would it be?
What is the funniest thing you have ever done or said?
Have you ever been caught naked by someone?
What is your funniest childhood memory?
Are you more of a night owl or a morning person? This is one of the questions to ask a guy that will lead to more questions and make the conversation flow smoothly.
What’s your greatest fear?
What do you believe I am thinking right now?
What nickname would you give me based off my personality or a body part?
While in school, did you ever cheat on a test?
If you could read minds, whose would you want to read?
If you were told you only had one week left to live, what would you do?
Which animal do you consider to be the sexiest?
If we were stranded on an island with no food, would you hunt to help us survive?
Which famous celebrity would you like to date, and why?
If there was only one cookie left, would you give it to me?
If there was only one cookie left, would you share it?
Would you rather race me on a jet ski or have I on the back of yours?
If you could feed me a dessert, what would you pick?
If I could be your passenger in any car or vehicle, what would it be?
What would the title of your autobiography be?
If you could have any kind of cake made for you in any size, shape, or color, what would it be?
You have three wishes from a genie. Go!
If you could go back in time, but only to last week, what moment would you visit and why?
Hotdog or hamburger?
Cookie dough or cookies?
Ice cream or milkshake?
Coffee or tea?
You can only wear one thing for the rest of your life. What do you choose?
If you could choose to be talented with words, music, or dance, what would you choose?
What celebrity most resembles me?
If you could go anywhere right now, where would you go?
If money were no object, what would you have for breakfast every day?
Would you rather live in a cave or under the sea?
Romantic Random Questions to Ask a Guy
What does it feel like to you when we hold each other?
When did you first realize you loved/liked me?
What is your first thought in the morning when you wake up next to me?
If we got married someday, where would you want to take me on a honeymoon?
If I had to move away really far, would you come with me?
How do you feel when we’re apart?
If I had to move really far, would you stay in a long distance relationship with me?
Do you believe in love at first sight?
Do you believe in soul mates?
Would you meet my parents?
Do you think we’re soul mates?
Would you introduce me to your parents?
Would you shout my name to the world?
Everything happens for a reason—why do you think we met?
What was your very first impression of me when you first saw me?
What was your first impression of me when we actually met?
Do you remember the day we met?
How would you describe our first kiss?
At what point did you decide that you wanted us to be “official?”
Is there a song that you think of when you think of me?
Why do you like/love me?
How old were you when you had your first kiss and what was it like?
Do you lead your life with your heart or your head?
Have you ever experienced a major heartbreak in a romantic relationship? Details?
What do you feel is the sexiest part about yourself? Physical and mentally?
What would you say is your idea of romance?
What part of the female body are you most attracted to?
Do you prefer candlelit dinners at home or a fancy restaurant setting?
What is your ideal romantic night?
10 Ways to Really Get to Know Him
What would your preferred superpower be?
If money was no object, where would you live?
Smart or happy? What is more important to you?
Would you rather ask permission with the risk of someone saying no or beg forgiveness later?
Are there things you are superstitious about?
What do you think people would say about you? Nicest things? Worst things?
What do you feel are your weaknesses?
What are your earliest memories?
Name the coolest place you went with your parents and what you did?
What was your worst job and why?
Flirty Random Questions to Ask a Guy
How many times did you want to kiss me before our actual first kiss?
Do you like kissing in the dark or kissing in the rain more?
How would you describe the way I kiss?
What is your favorite physical feature of mine?
What do you see when you close your eyes kissing me?
Would you rather hug for 5 seconds or kiss for 1 second?
Do you like to cuddle?
Would you kiss me on the nose?
Would you kiss me on the forehead?
Do you like when I touch your face?
Would you hold my hand in public?
Would you kiss me in public?
Where is your favorite place to be kissed?
Where is your favorite place to kiss me?
Would you ever go skinny dipping with me?
Would you ever take a bath with me?
Where is your favorite place to be massaged?
Would you kiss me on the wrist?
Would you kiss me on the neck?
Random questions to ask a guy over text
If you woke up tomorrow as Paris Hilton, what would be the first thing you would say to the press?
If you could kill someone just by looking at them, who would it be?
Have you ever spoken to a woman you were not attracted to, just because your friends dared you to?
Do you believe in a parallel universe?
What is the one thing that you would NOT like to change about yourself in your next birth?
Would you rather have an attractive gay man check you out, or an old stooping woman makes a pass at you?
When was the first time you lied to me?
Have you ever intentionally told someone another person’s secret?
How long do you think it would take for you to walk from the Earth to the moon?
Would you kiss someone just because someone agrees to pay you for it?
Between an intelligent woman who acts dumb and a dumb woman who tries to act intelligent, who would you pick?
Have you ever been attracted to an underage girl?
How often do you change your profile picture on Facebook?
If you were a girl, which of your present GUY friends would you like to date?
Do you think it’s alright if a woman pays the bill for a dinner that you’ve asked her out too?
Would you rather watch a recorded football match or go on a long drive with your girlfriend?
Have you ever gone up to a girl, talked to her and then realized that your fly was undone?
You say you love me, but do you LIKE me?
You’re marooned on a desert. You’re dying of thirst. A genie appears with just one sip of water and another mysterious liquid. What would you choose?
How would you react if you found out that your ‘girlfriend’ was actually a guy!!?!
What is the one word that you absolutely HATE people using?
Is there anyone in the world you love so much that you could give your life for them?
If you had the power to just utter a word and kill someone – no one would find out and you would not be charged with a crime, who would you kill and why?
Do you have a role model – someone you want to emulate? Whom do you admire the most?
Do you contribute to any charity? What is the largest amount you have ever given to any charity?
Are there any causes you strongly believe in?
If you won a million dollars in a lottery, what would you do with it?
If you knew you had only 2 weeks to live and death was imminent what the regrets you would have are? Why haven’t you done anything about those regrets? How would you spend those two weeks?
Is there someone from the past you really miss and would like to locate?
Who was your first love?
Who was the first person you ever kissed?
If someone gave you $1,000 and asked you to kill a butterfly by burning it alive in the flame of the candle, would you do it?
If you could take a year off a go traveling, where would it be?
Which sports do you play or watch?
Which is your favorite Comic book character? What do you like about him/her?
If you could relive the last five years of your life, what would you change?
Are you a virgin? Who did you lose your virginity to?
Do you watch porn? How would you react if you found your girlfriend or wife was into porn?
Are there any fears you have that you would like to get over?
Do you find yourself prejudiced or biased in any area?