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10 Random Questions to Ask a Guy

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10 Random Questions to Ask a Guy
10 Random Questions to Ask a Guy

10 Random Questions to Ask a 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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10 Random Questions to Ask a Guy

11 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.

1. Do you have any brothers or sisters?
10 Random Questions to Ask a Guy

22 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!

2. Do you have any ridiculous skills?
10 Random Questions to Ask a Guy

33 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.

3. Name one person who has impacted your life in an important ...
10 Random Questions to Ask a Guy

44 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!

4. What is your guilty pleasure movie?
10 Random Questions to Ask a Guy

55 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.

5. What is your favorite food?
10 Random Questions to Ask a Guy

66 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.

6. Who do you love most in the world?
10 Random Questions to Ask a Guy

77 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.

7. What is the funniest prank that you have ever seen or done?
10 Random Questions to Ask a Guy

88 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.

8. What is one characteristic in a mate that you find irresist...
10 Random Questions to Ask a Guy

99 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.

9. If you had all the resources in the world, and money wasn’t...
10 Random Questions to Ask a Guy

1010 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.

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