60 Random Questions to Ask a Guy


Communication is the intrinsic part of any relation and without proper communication, there will be a deterioration in the relationship. To keep the relationship successful, it is always a good idea to ask each other some random questions. It will help you to know some untold characteristics of your partner. This way you will start understanding each other and thus, it will help you to maintain a successful relationship. When you are on your first date with a guy and you are running out of a conversation, then some random questions may spice up the conversation. Sometimes, for the couple who are in deep love with each other, there are times when the conversation between the partners dries up and make the environment boring. So, do not allow these gaps to come in your relation and ask him some random but intriguing questions to make the atmosphere happening and get to know him and his personality!

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  1. Whom do you idealise?

This is a question which reveals much about any person! By the answer to whom he idealise, you can have an idea about his future goal and what he thinks about the surrounding atmosphere and society.

  1. What is your favourite food?

A man’s food choice, meal and the desert he takes says a lot about his personality. As an example, if he takes a sandwich for a meal very often then it says that he is an independent type of guy who is thoughtful and curious!

  1. How do you pass your free time?

How he uses his free time says a lot about his hobby and how does he react to his professional life. It also reveals how fun-loving your guy is when he is not working and when he is spending time with you.

  1. What would you do if you had a superpower?

A funny guy may come up with some weird answer to show off his sense of humour. If a guy gives an honest answer, such as; he wants to fly or he wishes to time travel or he intends to rectify some of his mistakes then it shows he is very responsible and always tries to be a perfectionist.

  1. Do you like pets?

If he straight away answers yes, then he is kind hearted and he cares about others. Any person who spends time with pets is kind hearted and generous.

  1. What is your favourite travel destination?

It will reveal much about the romantic nature of the guy. It will give you a chance to plan a good trip with your man!

  1. Do you like to walk alone?

If the guy answers yes, then he is a little introvert and may not be very expressive and vies verse.

  1. Tell me a joke you like

It’s the best way to find how humorous your date is. You may also see what kind of humour he is into. You are lucky if is not into any toilet humour!

  1. What talent you think is your strength?

A wise guy will answer this question smartly to show off his talent. It is a good chance to get to know about some hidden talent of your man.

  1. Are you a good cook?

A man who can cook is always sexy! Isn’t it? If he says yes then it’s a definite turn on! You can ask him to prepare something special for you on your next date!

  1. Do you like sports?

The choice of games can give you a firm idea if he is fun loving, active and holds a positive attitude or he is just a lazy and a boring guy!

  1. Describe your dream girl

It is an excellent chance to know what he traits on a woman. Do not try to compare yourself with his idea and remember that no one is perfect!

  1. Do like to dance?

If he says yes, then you can ask him for a dance with you! As you know, a man who can dance is a big turn on!

  1. What is your favourite ice-cream?

If you like ice-cream and love to share a talk when you have one, then it’s a good idea to know what kind of ice-cream he likes. You may surprise him with his favourite ice-cream while both of you are watching a romantic movie together! A taste of ice-cream also shows some fascinating characteristics.

  1. Are you active in social media?

If he says he uses the social media once in a while, then you know that life is much bigger than social media and he are not a time waster.

  1. Are you a phone maniac?

You do not want to date a guy who is addicted to phone and concentrate more on the phone than to focus on you!

  1. Can you describe your life in a word?

Well, this is a tricky question for anyone so spare him some time and if he uses a positive word, means he sees his life in a positive way and vice versa.

  1. Tell me one thing that you want to change about your past

If he answers that he intends to rectify any of the mistake done by him, then he is an honest guy. It’s a good thing to know about him on your first date!

  1. Do you have any dream car?

A taste of a car is a key to knowing a lot about him. If he loves old day’s classics then he has a classic taste and if he loves a sporty new car then he believes in adventure and he is modern.

  1. Do you lie?

This question may shock him a bit but if he is positive and answers the question without any hesitation then he is an honest guy if he says he lies when needed.

  1. Do you like to learn new languages?

You know he is romantic if he chooses French as a preferred language or he is very challenging if he chooses Japanese.

  1. Do you have any dream job and what it is?

If he answers to this question without any fumble, then you know that he has some goals and dreams in life and he wants to achieve them. On the other hand, if you realise he is making up a story, then keep a distance. Surely you do not want to go further with a guy who does not have any dreams!

  1. Where do you want to live in future?

Asking this question, you can identify your date’s dream home. If he desires to live in a place with beaches and party places, then he is a fun loving party animal! But if he desires to live in a hilly and beautiful natural location then he loves nature and silence.

  1. Do you like to fight?

Who wants to live with a guy who is into a fight very often or with a guy who is very short tempered? Let him justify the reasons for him being involved in a fight.

  1. Do you have any scar?

Well, a scar does not necessarily have to be from a fight. Sometimes a scar can be cool! At least, this will give a lot of things to talk!

  1. What kind of music you listen to?

This is a good question to ask as you will know a thing or two about your guy. You will be able to judge in what mood he is in most of the time.

  1. Do you have any fear of spiders or bugs?

This question is a catch. You can straight away notice if he is showing off his toughness or he is honest enough to express his fear. However, you want someone who is not afraid of these and who is tough and strong!

  1. What is your style statement?

It’s a great chance for you to figure out what to gift him on his next birthday! Find out if he loves casual or loves funky. You can also ask what styles he likes on a woman. This will give you a lot of idea on how to dress when you are with him.

  1. Are you expressive or shy?

Working out the friendship with a shy guy is an art and getting to know how shy or expressive he is, it will help you to get better in this art!

  1. Who is your celebrity crush?

Get to know about your date’s celebrity crush and why he admires that celebrity. But it is good for you if he is not obsessed with that person. You do not want to date a guy with some creepy obsessions!

  1. Do you have any favourite drink?

The way he answers the question will reveal if he is an occasional drinker or if he is an alcoholic. Surely, you are not going to go forward with an alcoholic! Let him know what you like to drink and how much you enjoy drinking.

  1. Do you have any favourite hairstyle on a woman?

If he is not bothered about the hairstyle much, then it’s good for you! If he praises your hairstyle and does not show any other preferences then also it’s good for you!

  1. Do you like to work out?

It’s a question where any guy gets conscious. You can straight away catch it if he is faking. If he says he is a regular gym guy, then ask him to show his abs! That’s a good chance to start a funny conversation.

  1. What would you do if you suddenly win 1 million dollars?

This is another old school but a good question to know how generous or ambitious your guy is. If he says he wants to give it back to the community to do something good for the society, then he is a catch!

  1. Do you like a conversation with any stranger?

If he says yes, then it’s good for you and it shows that he is open to any discussion and he is not choosy. But if he says no, then he may be an introvert type of guy.

  1. How do you want to be remembered?

How a person wishes to be recognised speaks a lot about his moral and thinking process. It shows how responsible and honest the person is in his life. You can also tell how you want him to remember. This may stimulate some more conversations between you two.

  1. What you desire of?

Every person has some desires in life and it is always a fun to know those secrets about a person. Moreover, it can open up many scopes of further conversations. Do not get too personal or do not go into a career. Just keep it simple and share some of your desires too.

  1. Do you like long drives?

It is a good question to ask your date if you like long drive too! You can plan to go for a long drive with your guy which will help you to get to know each other better. Long drives are always romantic and always gives a chance to have some random and exciting conversations.

  1. Do you have any favourite book?

If he says yes, then there is a good scope to take forward this conversation and discuss some of your favourite book with him. Talking about stories and favourite books can quickly stimulate the connection between you two.

  1. Are you religious?

It can be a controversial question but it is always good to know about the belief of your date. Of course, do not try to go into a debate as this may create tension between two of you. Keep it straightforward and funny.

  1. Did you ever try dating online?

This question may make him a little afraid that if he is honest enough then he will share his experiences. You can also share your tragic online dating experiences to spice things up and to make the atmosphere funny and exciting.

  1. What turns you off?

You do not want to be a deal breaker of your date. Do you? If not, then it is a good idea to know what turns him off so that you do not make any mistakes.

  1. What cartoon character you see in me?

It’s a funny question to ask and it will lighten the environment. However, do not get offended by what he says as he will also answer this as a joke.

  1. Do you like reading magazines?

His taste in a magazine will help you to have a closer look on his likes and dislikes and hobbies. It will also unfold some of his desires! If you know what does it mean!

  1. What kind of snacks do you crave for?

It’s a way opener for you. You might be wanting to know his taste as you may have to cook for him sooner or later!

  1. Who inspires you most?

Getting to know who inspires him most will give you an idea about the kind of person he is or he wants to be.

  1. Which animal do you like the most?

The kind of animal a person likes says a lot about their personality. For instance, if he like a lion then it means he is fearless and very outgoing. If he likes the dog, then he is generous and kind-hearted or just awesome.

  1. Are you an early morning riser or a late night owl?

It is an excellent question to ask as the habit of sleeping of waking up should not clash with you two.

  1. How tall are you?

It’s another embarrassing question for any man who is not very tall. Ask this question in a playful nature and make sure that he is not offended.

  1. Do you like your job?

It’s a question from which you will eventually come to know if he is happy with his life and confident or he is frustrated and thinks negatively about his job/life.

  1. Have you ever been banned or arrested?

It’s a good thing to know about the guy you are dating. Let him explain the circumstances and the reason for such incidents if happened any. Don’t be judgmental and declare him a criminal straight away. If he has been banned from a public place due to misbehaving or because he theft something, then run! You don’t want to be around a thief.

  1. Can you play the guitar?

Girls are crazy for the guy who can play the guitar! So, it’s your chance to know if your man can play and if he says yes, then ask him to play something for you. If he likes to play and is not faking, then he will play something for you to make you flatter.

  1. Are you a party animal?

Any guy who is a party animal may give less priority to your plans and may get bored easily from a romantic candle light dinner!

  1. Would you perform at a karaoke night if asked to?

A guy who has a lot of self-belief and who is not afraid of being judged will go on stage and perform without any hesitation. He is also very spontaneous and fun loving.

  1. Do you like coffee or tea?

It’s your chance to know his priority so you can surprise him with his favourite beverage anytime soon!

  1. Are you a family man?

If your guy says yes, then it means that he values the family time and loves spending time together. Here he will give a hint if he has any kids or was he in a serious relationship before.

  1. Do you love giving gifts?

Well, if he says yes, then it is a jackpot for you. You know that there are many gifts and surprises are going to come in the way!

  1. What can you die for?

You may want to know his extreme desires. Every person has something to die for. It may be their goals or may be something else personal. If there is anything or anyone for what or for whom he can die, then it’s a good thing to know beforehand.

  1. Share the worst date experience of your life

It’s an opportunity to have some laughter. You can understand what he likes or dislikes and how he behaves or reacts to certain situations. It may help you not to make the same mistakes.

  1. Do you have any favourite childhood memory?

Again, it’s a chance to open up many more conversation from this question. If he had a fun growing up, then he would be excited to share one or few of his favourite childhood memory with you. You can also share some of your crazy childhood memories to spice the things up.

Well, ladies here is the end of the 60 random questions to ask a guy. Hopefully, you will carry these questions in your mind and will use them when needed. But make sure he does not feel that he is giving a job interview in front of some strangers in the panel! Get him to feel comfortable and ask the questions in a funny and exciting way. Include your experiences with all the answers he gives to show that you have been to similar situations in your life as well. If you don’t want him to run away, then do not just shoot all the questions to him! Be wise and keep the environment happening and lightened.


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