31 Good Questions to ask a Guy


Approaching the opposite sex can sometimes be challenging and somehow be tricky especially if you are too shy or you were not yet properly introduced to the guy yet. But hush now darling, the journey of a thousand miles all begins with the first step and today, we will help you make this first step! Here are some good questions to ask a guy and keep your conversation going.questions to ask a guy

Ice Breakers and small talks

If you have a guy you secretly have a crush on and wanted to talk to him badly, here are some proven good questions to ask him without looking too flirty. Who knows, maybe a single ice breaker question is all it takes to form the relationship you’ve been dreaming of!

  1. What time is it?

Cliché as it may sound, but this is a classic and effective conversation starter. When asking, make sure you don’t have a watch with you or a clock nearby so that you’ll not be embarrassed in case he sees them around. Keep the ball rolling by asking follow-up questions and remember to make the conversation flow sound natural as much as possible.

  1. Where did you buy that…?

The technique here is to be attentive to details. Ask him where he bought the limited edition item he’s wearing or carrying. Then, try to add other details or a back story why you noticed that item (for example, you’re a fan of Bruno Mars too and you see him wearing a Bruno Mars shirt). Girls are naturally inclined with shopping so the guy will not suspect that you’re trying to hit on him by just asking this. Just don’t overdo it. Don’t weave stories that are not true and unrealistic.

  1. Do you like…?

This is a good follow-up question that goes with “where did you buy that…”. This also goes with what he is currently doing when you talk to him. For instance, if you caught him in an arcade playing video games, ask him if he likes that video game and then you may follow it up by asking who’s his character in the game, which version of the game he likes best etc.

  1. Where did you get that?

This goes hand in hand if you see a noticeable feature on him (e.g. scars, wound, marks, etc) but let me warn you. Don’t ask this question if the guy appears to have a dark gloomy personality. You don’t want to end up being chased away saying that “it’s none of your business”, right?

  1. Do you go here often?

Another timeless pickup line! This is often used when clubbing and partying but actually, this can extend to as far as your favorite coffee shops, community libraries, restaurants and parks. The options are endless!

  1. Which cologne do you use?

We are all stimulated by our senses and our sense of smell is probably the most sensitive of them all! So, if a guy smells heavenly to you, don’t be afraid to voice that out and start a conversation with him by asking which cologne or perfume he uses.

  1. Do you work here?

If you are in another office or establishment and noticed that the guy looks like he’s working there, ask him if he does work there. Sure, this is like stating the obvious but this is a good conversation opener especially if you want to know his name and be friends with him.

  1. Where did you got your name?

Start this question with a good introductory sentence. For instance, you may add this after: “Your name’s really cute” or “You have a nice name” or “Are you a German?” (If his name sounds German). This question would also work if the guy has a unique name that captures anyone’s attention.

  1. Can I borrow your…?

Pen is probably the most borrowed object aside from money. To start a conversation with a guy, try to be creative and make sure you borrow an item being called for in the situation you are in. For instance, if you are at the university and like this geeky guy, you may borrow his notes or eraser or whatever. Just remember to return them once you are done and get ready to initiate a conversation with them.

  1. Do I know you?

This works if you see a colleague or a batchmate you have been silently liking from afar in a place or event outside your organization. For instance, you see that guy you have a crush on in the mall and you noticed that he’s alone, you may approach him and say, “Excuse me, do I know you?” If he does know you, he will acknowledge you but if not, don’t lose hope. Ask him if he’s from your office or school or church because he really looks familiar. Then, get ready to talk to him and ask things that are both related to you.

On your first date

  1. What do you do?

This is one of the good questions to ask a guy on your first date. Of course, you would want to know what your guy does for a living and if it is decent enough (you don’t want to be associated with bad guys for sure!) for you to keep hanging out with him in the future. When follow-up questions after this are made nicely, this could lead to a series of topics and can prolong the convo further!

  1. When’s your birthday?

This is synonymous to the infamous “how old are you?” question. Sure, age should not matter but it is definitely a factor especially when choosing which topics are relevant, which jokes are laughable and which things do you and the guy you like both relate to. Plus, if you’re into astrology, now is the time to fish for details and see if the stars are with you.

  1. How many are you in the family?

Relationships and friendships are not just between the two of you so better to know how many they are in the family, who are his parents, siblings, etc. Who knows, your MBA professor might turn out to be his dad!

  1. What’s your birth order? (How is it being…?)

They say birth order has a psychological impact on each one of us. Find out his birth order and see if you both have complementing perspectives in life. Once you get to know his birth order, ask him how is it like to be an only child (if he’s an only child or middle child if he is) and you’ll get surprise how this can spring to a lot of conversation topics.

  1. What are your interests?

Ask him his favorite sport or hobbies and try to find something common to both of you. After all, romantic and platonic relationships are formed when you share the same interests together.

On your next date

The first date is all about profiling the other party, getting to know him better and finding out whether the two of you are a match made in heaven. Of course, same goes for the other party. Here are some good questions to ask a guy on your subsequent dates:

  1. What’s the best part of your job?

After asking him about his job on your first date, it’s now to get to know what kind of person he is by asking him the best part of his job. Through this question, you will be able to assess if he’s enjoying what he does and truly loves and knows his craft well.

  1. What do you do when you are bored?

Life is not always as bright and as exciting. When things turn dull, you have to know what your guy does to make life more bearable because it’s when things are dull and grey that you get to know what a person is really like especially his attitude and outlook in life.

  1. What is your favorite dish?

The way to a man’s heart is through his stomach. Ask him his favorite dish so you can cook them and find your way to his heart.

  1. What is your motto in life?

His motto reflects his goals and passion as a person. Find out if you share the same goals and passions in life.

  1. If you can go and live anywhere in earth, where would it be?

You may rephrase this as “Where’s your dream destination?” especially if you have  a traveler’s foot and loves to travel a lot.

  1. What’s your talent?

Just in case he did not elaborate it yet when you asked him about his interests, ask him what his talents are. You might be surprised to know that the apple of your eye is actually very talented and can pass as a contender for the Got Talent show.

Additional Questions to Keep the Ball Rolling

Curious about his principles in life? Want to know his perspective and take on things? Or just want to keep the ball rolling? Here are additional bonus questions you can ask him/

  1. If you will become a girl one day, what’s the first thing you will do?

Aren’t you curious to find out his version of Beyoncé’s famous song?

  1. When you were a young boy, what did you want to be when you grow up?

Find out what did it take for him to achieve his goals when he was younger. In case he didn’t become what he wanted when he was a young boy, this question will enable you to get to know how he lived his life together with the reasons for the detour or his change of his heart.

  1. How do you see yourself after 5 years?

Find out if your guy is a goal setter and sees the future in a bigger picture. Also, get to know if you share the same vision and whether the relationship can blossom into something more meaningful that transcends intimacy and romance.

  1. What was your most embarrassing moment?

Among the good questions to ask a guy, this is one of the most interesting. Find out how your guy took the embarrassing moments in his life and how he handled them. Another thing, this is also a measure of closeness or intimacy because a guy won’t share his embarrassing moment to you if he doesn’t trust you or you weren’t close enough.

  1. What’s your ideal girl?

You don’t have to be his ideal girl but admit it, at the back of your mind there is already a mental checklist whether you match his standards or not.

  1. Which places have you been through?

Find out if he has itchy feet (of course, just figuratively!). Ask him about the places he had been. You’ll be surprised where the flow of conversations can go just by asking his experiences on these places.

  1. Among the Marvel Heroes, who is your favorite?

Iron man, Captain America, Thor, Spiderman — Who knows he may even have a liking on Black Widow? Don’t forget to ask him why that Marvel hero is his favorite.

  1. If you can give an award to any person in your life, what award would be it and why did you choose that award?

This seems a cheesy question but actually, the goal here is to get to know the people that matter to him.

  1. What is the essence of being a man?

This was a modified version of a question asked to a Miss Universe before. Aren’t you curious how he would answer this on his own and how witty he could be? Who knows, maybe he’s a pageant material too!

  1. What’s your greatest fear?

Any man regardless of how strong he is on the outside has his own fears. Our fears are reflections of what we value in life so this is a good question that will reveal your guy’s priorities and what he deems important.


Please enter your comment!
Please enter your name here