Fun Questions To Ask A Guy To Get To Know Him

Medically reviewed by Andrea Brant, LMHC
Updated June 10, 2024by BetterHelp Editorial Team

When you first meet a guy you're interested in or go on a first date, it can be challenging to come up with questions to ask him. If you have a list of questions, you might forget them due to nerves. Understanding some of the most common conversation starters and practicing them before your date may help you prepare for the conversation. In addition, if you experience anxiety about dating and socializing, you can take a few additional steps to prepare for a fun and anxiety-free date. 

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Questions to ask a guy

Before and during your date, you can take a few steps to prepare for a healthy and fun experience, including the following. 

Prepare in advance

Before the date, prepare for how you want to interact with the guy. Think of a few questions you want to ask and write them down. Write down as many personal, random, or funny questions you can think of, then choose the best questions when you are done. After considering these questions, practice them in the mirror and try to solidify them in your mind. Studies show that writing down your thoughts can increase the chances of remembering them and succeeding at your goals.

Try to keep in mind that your date may ask you questions too. Avoid treating the date like an interview and ask questions in intervals. Open-ended personal questions can be beneficial for kickstarting a conversation. If the conversation flows naturally, consider putting your questions aside to focus on the moment. 

Consider your values

When thinking of questions to ask, consider your values when dating someone new or looking for a relationship. Consider the morals, values, or traditions you're most interested in learning about in this guy. For instance, if you are adventurous, you can ask, "What is your favorite thing to do for fun?" or "What is the most adventurous activity you have ever done?"

Ask open-ended questions

It can be helpful to avoid asking closed-ended or "yes-or-no" questions. For example, you might want to know if your date likes traveling. Instead of inquiring, "Do you like to travel," consider saying, "How do you feel about traveling out of the country?" or "What is the coolest place you’ve ever been?" or “Where would you go on a week long adventure?” By inquiring about more open-ended concepts, you may allow your date to respond with more information, including their thoughts, feelings, attitudes, and beliefs. 

Another potential benefit to asking open-ended questions is that your date may feel less like they are at a job interview and instead feel like you are connected and participating in a mutual conversation. Note that a first date is not an interview or an interrogation, so try not to feel overwhelmed by the ideas you have written down. The conversation between you and your date may flow freely and organically. 

How to cope with social anxiety while dating

According to Dr. Thomas Richards from the Social Anxiety Institute, social anxiety is "the fear of being judged and evaluated negatively by others, leading to feelings of inadequacy, inferiority, self-consciousness, embarrassment, humiliation, and depression." 

Dr. Richards explains that individuals who feel "anxious in social situations but seem better when alone" may struggle with social anxiety. For these people, the thought of going on a first date and meeting someone new can be emotionally taxing and exhausting. Consider the following techniques if you feel your social anxiety "taking over" during a date. 

Take a break

Whether you briefly step outside for a breath of fresh air or go to the bathroom for a couple of minutes, taking a break and stepping away from the date may be helpful. Let your date know you're going to make a phone call or need to use the bathroom and reassure them you'll be back when done. 

Skip the silence

Depending on your level of anxiety, your date may notice your nervousness. If you are comfortable doing so, find a casual way to acknowledge your anxiety. You might say, "I'm having a lot of fun, but I feel nervous." By making this statement, you have taken control of the anxiety and taken some of the secretiveness away from it. It may open the door for a new conversation and allow you and your date to feel less tense, stressed, and nervous. Your date might also have anxiety, showing you that you're not alone. 

Stay focused

Be present and pay attention to the conversation. Instead of thinking, "What are the other questions from my list?" or "I wonder if he notices how nervous I am?" try to remain focused on the conversation. Doing so could make you appear interested in what your date is saying. In addition, you may feel more prepared to answer the questions they have for you. 


Questions to ask a guy to get to know him

You can use many questions on a first date or with a guy you just met. Below are a few ideas. 

Conversation starters

Starting a conversation can be intimidating, whether through text, social media, or real life. A conversation can be a kick-starter for closeness and vulnerability in the dating world. Write down a list of topics that would allow the conversation to flow. A few questions you can ask include the following: 

  • What is your passion?
  • What is the best advice you’ve ever received?
  • What is a surprising thing about you?
  • If you could change one thing about the world, what would it be?

Consider skimming a guy's dating bio and asking questions about their interests. For example, if the guy is into animation, inquire about their favorite cartoon. 

Depending on their openness, a conversation starter could be a more profound or personal question. For example, you may ask a guy to tell some embarrassing stories. To start the conversation, try revealing an embarrassing story of your own.

Date questions to ask

Asking a guy engaging questions about varied topics (such as his dream career, childhood best friend, or favorite movie) can help you learn more about his personality and find out how compatible you may be. Below are random questions you can ask a guy on your first date. 

  • What was the worst job you’ve ever had?
  • What's your favorite childhood memory
  • Tell me about the most embarrassing thing that’s happened to you.
  • What's your favorite family memory?
  • What’s your dream job?
  • Would you say that you're a morning person or a night owl?
  • What are you most likely to buy when you spend money for fun?
  • What's one food you hate and one food you love?
  • Are you a dog person or a cat person?
  • How did you meet your best friend?
  • What’s the most useless advice you’ve ever gotten?
  • What’s your favorite meme?
  • What's the weirdest flavor combination you enjoy?
  • What’s one of the funny stories you always tell?
  • What’s the worst pickup line you’ve ever used?
  • What’s your favorite pickup line?
  • What's a fun activity you want to try but haven't done yet?
  • What's on your bucket list?
  • If you were stuck on a deserted island, what three things would you bring?
  • What's one song you could listen to repeatedly?
  • What is your most prized possession?
  • In your opinion, what's the funniest movie?
  • What's your idea of a perfect Saturday night?
  • What’s your favorite video game?
  • Who is your favorite person to spend time with?
  • What's your favorite movie?
  • What's your favorite food?
  • What's your weirdest habit?
  • Tell me about your worst date/best date.
  • Do you have a favorite physical feature in other people?
  • If a girl makes you dinner, what would you want her to cook?
  • Do you remember your first crush?
  • Would you say that you're a competitive person?
  • What's your wildest sex story?
  • What’s your favorite sex position?
  • Do you think you have ever broken someone's heart?
  • Do you believe in the concept of soul mates?
  • Tell me the story of your first kiss. 
  • What’s your biggest fear?
  • What's the weirdest thing about you?
  • What would you say your best physical feature is?
  • What's the scariest thing you've ever done?
  • Would you survive a zombie apocalypse?
  • Is there a family you don't get along with? Why? 
  • What's something you want to know about another person by the third date?
  • What's your biggest pet peeve?
  • Do you know your love language?
  • How did your last relationship end?
  • What’s your “go to” joke?
  • What's your guilty pleasure?
  • Who would you trade lives with for a day if you could?
  • What's a recent embarrassing moment you had?
  • What are three words that describe you as a romantic partner?
  • What's your biggest regret?
  • What’s your best pizza in town?
  • What do you think makes a healthy relationship?
  • What would you tell your younger self?
  • Can you ever stay friends with an ex?
  • Do you consider yourself a spiritual person?
  • Tell me about one memory that shaped you as a person.
  • What puts you in a good mood?
  • Tell me about your typical day.
  • What is your favorite movie genre? 
  • When was the last time you laughed so hard that you cried?
  • What was your favorite cartoon or fictional character as a child? 
  • What's the best or worst hidden talent you have? 
  • What is the craziest thing you've ever done? 
  • Who is your biggest hero? 
  • Do you have to fall asleep with the TV on?
  • What’s the biggest life lesson you’ve learned?
  • What would you do if you had a million dollars? 

Flirty questions to ask a date

When you like someone, asking the right questions can be one of the go to flirting techniques you can use to get to know them while increasing your connection. Below are a few questions to get started:  

  • Have you been working out?
  • 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?
  • Where would you take me if we won enough money for any romantic date? 
  • What do you think of our connection so far? 

Thought-provoking questions to ask a guy you just met

Deep questions may help you reach a level of vulnerability with someone you just met. Below are a few questions you can use to get started:  

  • If you could go back ten years and tell yourself something, what would you say?
  • 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?

Deep questions to ask a guy can range from politics to philosophy to open-ended questions promoting conversation. One way to get deep is to have a comfortable environment. For example, lying down in the grass and looking at the stars is one way to increase your connection.

Explore dating anxiety and social interaction with a professional
Support options

If the stress of a first date or socializing with someone new makes you so anxious that you have difficulty functioning in other areas of life, you might be experiencing social anxiety. People living with social anxiety disorder often benefit from professional support, which can effectively treat symptoms. However, some people with social anxiety fear contacting an in-person therapist due to the social aspects of a face-to-face therapy session. 

Online therapy through a platform like BetterHelp may be a convenient option for those with anxiety or stress surrounding social situations. Through an online platform, you can choose between phone, video, or chat sessions. A chat session might be beneficial if you struggle to talk to others when anxious.  

Additionally, research has found promising results in studies on internet-based therapy. A recent study showed that even a brief online intervention could improve symptoms of social anxiety among adults. Another study found that online therapy through a chat platform could reduce anxiety symptoms and was as effective as in-person counseling. 


Coming up with questions for a first date with a guy can be exciting and stressful simultaneously. Consider the questions above for inspiration, and if you start to experience anxiety symptoms, you can also reach out for support. Online and in-person therapists can be effective forms of guidance as you learn to manage the symptoms of social anxiety and date-related nervousness.

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