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20 Random Questions to Ask a Guy

Random Questions to Ask Any Guy

Let’s be real. Dates can be awkward. The tension of wanting to impress your date, and hide how nerdy you actually are can get the best of us sometimes. For all the victims of awkward dates, there is hope. As women we’ve all been there, it doesn’t matter if you’ve been dating for a while, or if you’ve just started dating, here are fifteen questions to loosen up the conversation and get to know your man a little bit better.

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11 What is the weirdest thing that you ever did in high school?

This can be a fun way to get to know your significant other’s personality. The answers to this question could range from awkward stories, to hilarious confessions. This funny random question is a great way to start off the night, because it takes the awkward tension away from a situation, and replaces it with laughter and fond memories. Don’t be afraid to start off by embarrassing yourself, and sharing one of your own embarrassing stories from high school. The second that either of you stop feeling the need to be cool and collected around each other, is the moment that you will find true compatibility with your date.

1. What is the weirdest thing that you ever did in high school...

22 If you had all the resources in the world, and money wasn’t an issue, what would you do for a job?

This question is important because it will give you a peek into your dates dreams, and work ethic. The way that he responds will give you clues about his character, and lets him know that you are genuinely interested in who he is as a person. In this situation remember to be actively listening, and interested in what your partner is telling you. Dreams are extremely personal things to share, and tell a lot about a person. This is also a great way to find out about your date’s work ethic by finding out what steps he has done to accomplish his dream. You could follow up this question by asking him how he came to have this passion, and what he is doing now to pursue it.

2. If you had all the resources in the world, and money wasn&#...

33 What is one characteristic in a mate that you find irresistible?

Who wouldn’t want to know what their boyfriend likes? This doesn’t have to be something that he likes about your appearance, it can also be thing that he finds attractive of your personality. Does he like funny girls? Sarcastic girls? Don’t be afraid to ask him what he likes or doesn’t like in a mate. Remember that whether or not you fit his criteria that is not your problem. Don’t change yourself to be liked better by a boy, but look for the things that he finds attractive, and that you naturally possess.

3. What is one characteristic in a mate that you find irresist...

44 What is the funniest prank that you have ever seen or done?

This is a great way to break the awkward tension, and find out what makes your date laugh! Sharing funny memories makes any situation easier to navigate. Make sure to notice if your potential boyfriend was watching the prank happen, or he was making the prank happen. This could be a sneak peek into his personality, and the dynamics of his friendships.

4. What is the funniest prank that you have ever seen or done?

55 Who do you love most in the world?


Don’t be afraid to talk about the important stuff as well as the fun. A great rule of thumb is to ask questions that focus on important aspects of the other person’s life, and try to divert the conversation back to them. A huge part of dating is being able to listen. Ask questions about his answer to show that you are interested in the people that he cares about.

5. Who do you love most in the world?

66 What is your favorite food?

Ever heard the saying, “the best way to a man’s heart is through his stomach?” Ask this question and cook it for him for a second date! This is a great way to show that you are able to take care of your potential man, and he will definitely appreciate it.

6. What is your favorite food?

77 What is your guilty pleasure movie?

Everyone has a movie that they don’t want to admit they love. This could range from “The Notebook” to “Legally Blond.” Whether or not your date tells you the answer to this question depends on how comfortable you are with each other. Pay attention to whether or not this is something that is easy for him to confess. The easier it is for him to confess a potentially embarrassing story the more confidant he is. Make sure to confess your own guilty pleasure as well!

7. What is your guilty pleasure movie?

88 Name one person who has impacted your life in an important way?

Some of these questions may not work if you’re on a first date, but it doesn’t hurt to ask. This question could be an easy way to get to know the more serious side of your date, and understand how he views the people in his life. Gratitude for people who have encouraged and poured into one’s life is a very important characteristic for a mate.

8. Name one person who has impacted your life in an important ...

99 Do you have any ridiculous skills?

This is such a great way to get to know the fun side of your date! These skills can range from playing the banjo, to juggling, but they are guaranteed to make the night more interesting. Make sure to share your own quirky skills, and if able, display them!
What is your favorite board game?
You could easily plan a date based off all of the answers to these questions. Make his favorite dinner, and play his favorite childhood board game. Try to mention your own, and be competitive!

9. Do you have any ridiculous skills?

1010 Do you have any brothers or sisters?

Family is an important aspect of any relationship, and being interested in your significant other’s family will show you are invested. Ask questions about his brothers or sisters, and find things that you can relate to them with.

10. Do you have any brothers or sisters?

1111 Did you play sports growing up?

Men and sports are synonymous with each other. Ask questions about favorite sports that he watches or plays in. Questions like, “what is your favorite part of watching or playing?” can help you better understand whether he is active or not.

11. Did you play sports growing up?

1212 If there was one thing that you could change about your life, what would it be?

An important aspect of a relationship is pushing the other person to be the best that they can be. This means encouraging them to complete things that they have always dreamed of doing. Ask this question, and make sure to remember to always try to help your significant other succeed in his life and dreams.

12. If there was one thing that you could change about your lif...

1313 Do you like Sunny days or Rainy days best?

Ask this random question as a way to understand whether he is the type of guy to stay inside and cuddle all day, or bring you on exciting adventures outside! This question gives you a sneak peek into his personality.

13. Do you like Sunny days or Rainy days best?

1414 What is your favorite dessert?

Store the answer to this question away for special events later on, or you could impress him by making it for your next date!

14. What is your favorite dessert?

1515 What is your favorite type of music?

Someone’s choice in music tells a lot about their personality. From the classic creed lovers to the new age electronica devotees, you can better understand your man by knowing his music tastes.

15. What is your favorite type of music?

1616 What is your earliest memory?

Answers to this question show the sentimental side of your date, and can show you the important people and events in his life. This is a question that all people may not have an answer to, but in the case that it does, it shows you the inner workings of your date’s life.

16. What is your earliest memory?

1717 What is the weirdest job that you’ve ever had?

This question is a great way to get to know the quirky side of your date, and can show whether or not he is adventurous! Jobs are important because they show a level of experience, and the desire to succeed. Do his past jobs have ties to what he wants to do with the rest of his life, or are they fillers. Did the jobs add some type of new life experience? Answers to these questions show a willingness for adventure and success.

17. What is the weirdest job that you’ve ever had?

1818 What has been the scariest moment of your life so far?

Answers to this can range from serious moments of tragedy, to hilarious moments of triumph. It is important to know that everyone has their own fears, and that is okay.

18. What has been the scariest moment of your life so far?

1919 What is your favorite thing about yourself?

This could be the most important answer that you receive. Self-confidence is a must have attribute in a mate, and knowing the answers to this helps you to understand who the other person sees themselves as, and who they want to be. Remember to be confident in your own answer to this question. Knowing your own strengths and weaknesses is an important characteristic to have in a date.

When asking these questions remember that the most beautiful brand that a woman can wear is self-confidence. Be the amazing, beautiful person you are, and everything else will just happen.

19. What is your favorite thing about yourself?
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