Good Questions To Ask A Guy

By Sarah Fader |Updated August 5, 2022
CheckedMedically Reviewed By Carnell Colebrook-Claude , MA, NCC, BC-TMH, LPC (Clinical Track), LPCC, LCPC, LIMHP, LSOTP

Have questions? Prompting scripted ones to someone is fine online, but in person, you'll want to present things naturally. Continue reading for some advice and check out online therapy for additional information on how to tackle approaching guys in general.

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Feeling Butterflies, And Not Sure What To Say?

Wondering what things to inquire4 when you meet a new guy? The best thing is prepare. Think of some good ones that you would like to know the answers on and write them down. Write as many as you can think of and then choose the best ones when you are done. After all, you do not want to try to memorize 50 questions to ask a guy you just met!

Also, you do not want to bombard him with things so that he’s so overwhelmed he doesn’t know which one to reply to first. However, you do want to be prepared for the conversation, so you are not just sitting there with nothing to say. If the conversation is flowing naturally, put them aside and be in the moment.

Now let’s be honest, the idea of sitting down and jotting down some to ask a boy you just met may be easy for some people, but what if you experience writer’s block? Or what if you find yourself overthinking the process and writing down too many? You may want to start by considering what things are important to you when it comes to meeting someone new, dating, and being in a relationship. Consider some of the morals, values, or traditions that are important to you, and allow those factors to guide your list of first-date things to ask a guy. For instance, if you are an adventurous person or more of a “stay-at-home” type, you may ask things such as, “What do you usually do for fun?” or “What is the most adventurous thing you have ever done?”

It can also be helpful to stay away from inquiring closed-ended or “yes-or-no” questions. So, let’s say you want to know if your date enjoys traveling or not. Instead of inquiring “Do you like to travel?” – which would be a yes or no question – you may inquire, “How do you feel about traveling out of the country?” or “What is the best vacation you have ever taken?” By inquiring more open-ended things, you allow your date the opportunity to respond with more information, which may include their thoughts, feelings, attitudes, and beliefs. Less work for you! Another benefit to inquring open-ended things is that your date will be less likely to feel as though they are on a job interview, and instead feel like you are connected and are participating in a mutual and very interesting conversation.

Keep in mind that a first date is not an interview or an interrogation, so try your best not to become overwhelmed by the things or ideas you have written down. The conversation between you and your date should flow freely and organically, and it feels genuine.

Questions to Ask a Guy

Here are some of the top 10 things to ask a boy and why they are good to inquire:

  1. What makes you smile? Asking him this question will let him know that you want to know what makes him happy.
  2. What are your favorite kind of movie and her best fictional character? This will help you find out if you and he have similar interests. For example, if you both like horror movies you already have something in common.
  3. What was your favorite cartoon or fictional character in it as a child? Similar to the question about movies, this question can also lead to fun memories about his childhood.
  4. What’s the best or what’s the worst hidden talent you have? Let him talk himself up (or down) or make you laugh.
  5. What is your favorite car? Let’s face it: Many guys like to talk about cars. Let him know if you’ve ever heard of them
  6. What is your favorite sport? Just like the car question, boys like to talk about sports.
  7. What is the craziest thing you have ever done? This will help let you know what his boundaries are and what he is willing to do.
  8. What was the most frightening moment of your life? It is good to know what scares a boy.
  9. Who is your biggest hero? The answer will show you who he aspires to be. If he says it is his father, then you know he has a good relationship with his dad.
  10. What would you do if you had a million dollars? Knowing what he would do with a bunch of money can help you figure out if he is greedy or kind.

Social Anxiety

According to Dr. Thomas Richards from the Social Anxiety Institute, social anxiety can be described as “…the fear of being judged and evaluated negatively by other people, leading to feelings of inadequacy, inferiority, self-consciousness, embarrassment, humiliation, and depression.” Dr. Richards also explains that individuals who will typically become “(irrationally) anxious in social situations, but seem better when they are alone”, maybe struggle with social anxiety. For these persons, the very thought of going on a first date and meeting someone new can be emotionally taxing and exhausting. If at any point during the date you feel your anxiety is “taking over,” try any of the tips listed below:

  1. Take a break. Whether it is briefly stepping outside for a breath of fresh air or going to the bathroom for a couple of minutes, it may be helpful to take a break and step away from the date.
  2. Break the silence. Depending on your level of anxiety, your date may notice your nervousness. So, if you are comfortable doing so, find a casual way to acknowledge your anxiety. You can do this by saying, “I’m having a lot of fun, but I’m also a little nervous.” By making this statement, you have taken control of the anxiety instead of allowing it to take control over you. Also, it will likely open the door for a new conversation and allow both you and your date feel less tense, stressed, and nervous.
  3. Stay focused. Be present and pay attention to the conversation. Instead of worrying yourself with inner thoughts such as, “What are the other questions from my list?” or “I wonder if he notices how nervous I am?” remain focused on the conversation that is being had. By doing so, you can not only keep up with your date and respond appropriately, but you will look interested in whatever your date is saying.

No matter what questions you decide to ask him, be prepared to answer your questions as well. Be honest, do not pretend to be someone you are not or your relationship will never work. There are mental health professionals to talk to if you feel like you need to talk about it. You do not have to make an appointment or go to anyone’s office. You can just go to BetterHelp and talk to an online counselor right now.

Flirty Questions To Ask A Guy 

When you like a boy, one thing you can do to get close to him is to inquire things. In the context of flirting, all the types of questions come into play. Flirting can consist of funny things, random things, and especially personal things. With a boy, your questions should be blunter, but some boys may like a little ambiguity.

Here are some good questions to get you started.

  • “Have you been working out?”
  • “Who is the best kisser you’ve ever had?”
  • “If you could be with a famous person, who would you be with?”
  • “If you could pick an outfit for me, what would it be?”
  • “What would be the most romantic place you would visit if you could?”

20 Questions To Ask

In a game of 20 questions, a great question is something that narrows down the person, place, or thing the person is thinking of. For example, if someone is thinking of a person, a great question can be “Is this person still alive?” It can be “Is this person a politician?” Anything to narrow down what the person does and their features can help you guess. If it’s a place, a great question you may first inquire “Is it within 100 miles?” Deciding if the place is local, far away, or even on this planet can help you figure out where it is. And so on. It needs to be specific enough to narrow it down, but not too specific. The last question should be the guess.

Ask Deep

Deep, interesting questions can get to know someone better and encourage more interesting conversation topics outside of “What’s your favorite color?” here are some questions to ask people.

  • If you could go back 10 years ago and tell yourself something, what would you say?
  • Do you believe that we are living in a simulation?
  • If you could speak with any historical figure and try to get them to change their mind about something, who would it be?
  • What are five things you believe are flawless?

These are just a couple of examples. They can range from politics to philosophy to just open-ended questions that promote great conversation. One way to get deep is to have the right environment. As cliché, as it sounds, looking at the stars, can be a good way to promote deep conversation topics.

Starters To Try

Starting a conversation can be a nightmare, be it through text on social media or in real life. Just saying “Hi, what’s up?” can make people not want to talk with you. You often have to think of something to get that person’s attention. Funny things, fun things, deep things, a simple question, it can depend from person to person.

In the dating world, it’s important to have a good conversation. A dull conversation can spoil the date, even if the two of you are meant to be. Write down a list of best things that would be great conversation material. These best questions can include:

  • “What is your biggest obsession?
  • “What is something a person may not know about you upon first glance?”
  • “If you could change one thing about the world, what could it be?”
  • Some fun questions can include skimming a person’s dating bio and inquiring questions about their interests. For example, if someone is into animation, inquire about what their favorite cartoon is.
  • A great question doesn’t have to be serious, either. You can ask fun questions. For example, a good question maybe “If you had 10 bucks, what food would you get?”
  • Depending on the openness and how close you are, a conversation starter can be a more deep question, or something personal. For example, you may ask a person to tell some embarrassing stories. To start the conversation off, you may end up revealing an embarrassing story of your own?

Overcoming Anxiety

When you end up talking with a boy, your brain may turn to ice. One way you can talk is to ask questions. Think of a series of best questions and think about how you’ll go about inquiring that question. Fun is imagining the ways you can word a question. For example, instead of inquiring “What’s your favorite color?” ask “What color comes to your head when you hear the word ‘color?’” A mixture of his life and his beliefs are some things to talk about, but every boy is different.

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How To Attract Someone To You

Be yourself, but be the best version of yourself. Have a good laugh with each other and don’t be afraid to tease a little. Inquiring open-ended questions and have your crush a similar question. To the drop of a hat, respond to the best of your ability.

Also, flirt and push your intentions at the beginning. Some people talk endlessly without asking them on a date, then end up in what they refer to as the friend zone. Love questions are one way to avoid this, but you also should respect if someone doesn’t see you as a lover. There are many ways to get closer to a boy, and here are some ways you can do so.

  • Ask him great questions. When you’re on a date, questions that are open-ended and show a boy that you’re interested in can get you far. For example, one of the best questions you may ask is “What do you want in a person?” Another kind of question can be one that is more philosophical and it can give you an insight into what the boy believes.
  • When the boy talks, show interest. Asking a follow-up question can lead to the boy realizing you do care about him. If you don’t show any interest, there’s a good chance your relationship doesn’t go too far.
  • Give your boy the date of his life. While you don’t have to go someplace expensive, take him to a place he loves, and show you do care.
  • Ask personal questions, but the question with caution. Some boys may not want to open up, especially if they’re recently single. One way you can question with caution is to reveal something about you, such as admitting the worst lie you ever told. Truth or dare questions are another good type of question for finding more about a boy.
  • Express your interest to get closer and to know him better. If you’re upfront with him, there’s a good chance he’ll respond to that with positivity. Some boys do not take hints very well, and you want to make sure you’re on the same page as him.


No matter what questions to ask a boy you decide on, be prepared to answer your own questions as well. Be honest, do not pretend to be someone you are not or your relationship will never work. However, if you have significant trouble talking to people for the first time and the stress of situations like a first date make you so uncomfortable that making small talk and eye contact becomes too much to handle, you may be experiencing social anxiety and if you have it, there's hope. The toughest part of dealing with any issue is being able to ask for help. There are mental health professionals to talk with if you feel like you need to talk about it.

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