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20 Good Questions To Ask A Guy

First dates are tough. They can be awkward and uncomfortable because getting to know someone new is almost always difficult, especially with the added pressure of potential romance. Fortunately, coming into a first date prepared will help you out big time.

Use the 20 good questions to ask a guy guide below to make your first date really count.


Question 1 – What makes you smile?

Asking a guy a question like this one on a first date is a surefire way to make him smile! It will also help you find out what he is interested in and passionate about for future reference.
Question 2 – What do you like to do with your free time?

A question like this one also helps you figure out what a guy is all about.
Question 3 – What is your most embarrassing moment?

The great thing about asking a guy about his most embarrassing moment is that it shows you a bit more of his personality. It also gives you some pretty good flirting material for the future! Playful teasing is almost always fun.
Question 4 – What is your favorite sport?

Sure, it is something of a stereotype, but most guys like to talk about sports.
Question 5 – What is your favorite food?

First dates are all about getting to know the other person. Asking “favorite” questions are just so great because they help you do this.
Question 6 – What was your worst haircut?

Laughing and having fun is an important part of a first date. Asking a guy what their worst haircut ever was is sure to make both of you chuckle (or cringe!).
Question 7 – If you could travel anywhere in the world, where would it be?

A question like this one shows a guy that you are actually interested in him. Plus, it is interesting to find out what places a person that you like loves to visit.
Question 8 – What is your perfect day?

Asking a guy this question has so many benefits. First of all, it is an interesting question that will warrant plenty of conversation. Secondly, it can help you find out what your guy likes the most. You can then use this info later on to plan a special day for him (if your dates keep going well!).
Question 9 – Who is your celebrity crush?

Another fun question, asking a guy who their celebrity crush is can help you find out what kind of girls they are into!
Question 10 – Are you a cat or a dog person (or neither)?

First dates are all about having fun. This question is all fun and could lead to some playful arguing if you take opposite sides.
Question 11 – What is your biggest pet peeve?

While your first couple of dates should be mostly about having fun, there is no reason you can’t dig a little deeper to make sure you actually like the guy you are seeing. Asking a question like this one will help you find out more about who your guy actually is.
Question 12 – Do you have any nicknames?

Nicknames can tell you a lot about a person. So ask this question and find out!
Question 13 – Where do you see yourself in five years?

Another deeper question, asking a guy where they see themselves in five years can help you find out if you are compatible. It will help you dial in their interests and can lead to a lot of future conversations.
Question 14 – What did you want to be when you grew up when you were a kid?

This question is similar to the one above. It will also be fun to compare their two answers.
Question 15 – What’s the first thing you’d save in a fire?

Knowing what a guy holds important to them is good to know. Asking what they’d save in a fire will help you find out.
Question 16 – What is your worst habit?

It is good to find a guy that knows himself well and isn’t embarrassed to talk about his negative side. This question will help you make sure that you two are a solid match.
Question 17 – What is your favorite movie?

Keeping the conversation moving is essential on a first date. Asking what their favorite movie is can help.
Question 18 – What is your favorite book?

This question is also a good one to ask to keep a conversation from stalling. You might also find that you have literary interests in common!
Question 19 – Who was your first crush?

A fun question that takes you back to childhood, asking a guy who their first crush was is just fun and interesting all around.
Question 20 – Do you want to see me again?

It might be nerve-wracking but asking a guy if they want to see you again at the end of your first date is essential. I mean, how are you going to know otherwise?

BONUS – 30 more questions to ask a guy.

Question 21 – Do you consider yourself a player?

The answer to this may make you want to move on.
Question 22 – Do you get along with your parents?

Gives you information about his family and how they operate.
Question 23 – Does he like his job?

Icebreaker and indicator about his future plans.
Question 24 – How was your day?

Good way to really get to know somebody based on how he answers.
Question 25 – What kind of car do you drive?

A superficial question but loaded with answers.
Question 26 – Do you have any brothers or sisters?

A good icebreaker, will help him relax and help you get to know him.
Question 27 – Do you like rainbows?

Can help tell how deep he is.
Question 28 – What is your favorite scene in the movie “Forrest Gump”?

Breaks the ice and can make you both laugh.
Question 29 – What is your favorite kind of ice cream?

Loosens him up and makes you both laugh.
Question 30 – Does he want children like you do?

This may be a good way to narrow down the gene pool, and make you both happy.
Question 31 – What kind of beer do you like to drink?

Gives you insight into his tastes.
Question 32 – Do you like to hike?

Indicates what kind of activities he likes to do, he may not like to ruff it.
Question 33 – Do you have any hobbies? If so what are they?

A way of getting to know him.
Question 34 – Do you like the President?

A way of seeing what kind of beliefs and principles he stands on.
Question 35 – Do you like quiet or out on the town evenings?

Shows that your lives are compatible.
Question 36 – Do you consider yourself religious?

A must question for those that have strong religious beliefs.
Question 37 – Do you like comedies or dramas?

A good personality measurement, is he is serious or fun loving.
Question 38 – How close are you with your family?

Tells you about his character.
Question 39 – Do you like to fly?

Is he transient or a homebody, this question may answer that.
Question 40 – What do you like to do with your off time?

Helps him relax and get to know him.
Question 41 – What is your favorite space or astronaut memory?

To find out if he likes science or exploration.
Question 42 – Do you have a smartphone?

How much he loves or hates technology.
Question 43 – Have you rode the Space Mountain roller coaster?

See if he is a bit of a daredevil.
Question 44 – What was the last movie you saw?

To converse and put you both at ease.
Question 45 – What road trip have you taken lately?

For conversation and to see if he is interesting.
Question 46 – What do you think of the show; “Modern Family”?

To start a conversation and see what his views on family are.
Question 47 – What is your personal philosophy?

To have a laugh or serious conversation.
Question 48 – What do you do for fun?

To break the ice and learn more about him.
Question 49 – What kind of kid were you?

To learn more about his personality.
Question 50 – What is your heritage?

To provide stimulating conversation and learn more about their history. You can possibly connect on your family histories. You could also start a great relationship just being interested in each other’s family history or ethnic group


We hope you enjoyed our favorite 20 questions to ask a guy plus the 30 bonus questions. These questions should be exactly what you need to make it through a first date with flying colors – and then hopefully on to a second!

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