20 Really Cool Questions to Ask a Guy You Like

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questions to ask a man you love

If you have your eye on a guy, but you really haven’t gotten to know each other yet, asking questions is a great way to get closer and find out how compatible the two of you are.

There are, literally, hundreds of questions you could ask, but we’ve rounded up 20 really cool questions that will give you some insight into what kind of guy he is.

1. “What makes you smile?”

Asking him this question will let him know that you’re interested in what makes him happy. It will also give you an idea of the nature of his personality. If things work out with him, you can use his answer to make him smile in the future.

2. “If you could go anywhere in the world, where would you go?”

Asking this question will help you get to know him a little bit better. Who knows, you may even share the same dreams of traveling the world together.

Asking this will also give you some insight into his personality. For example, if he answers with Vegas or Cancun, he may be a party-goer who likes to have fun. If he chooses his family’s home country, it shows you that he values his family and where he came from. Pay close attention to his answer to see what kind of guy he is.

3. “What’s your favorite car?”

This is a question he won’t mind answering. Most guys love cars, and he’ll appreciate you asking him about things he’s interested in.

4. “What’s your favorite food?”

This is another question that will help you get to know him better. His answer will also come in handy when picking a place to eat or if you decide to cook him dinner one night.

5. “What’s the first thing you notice about a girl?”

Asking this question gives you a chance to get a little bit flirty with him. It will also give you an idea of what kind of guy he is, and what he likes most about a girl.

6. “What’s the craziest thing you’ve ever done?”

This question will get him to engage in a conversation about some of his life experiences. How he answers this question will tell you a lot about his personality and what he likes to do in his free time. If he says that he bungee jumped off of a bridge, for example, you know that he might be an adrenaline junkie.

7. “What are your favorite hobbies?”

His answer will help you gauge how compatible the two of you are, and also helps you get to know him a little bit better. Who knows? Maybe the two of you share the same hobbies.

8. “If you had one week to live, what would you do?”

This is an interesting question to ask and can spark up a conversation. His answer will give you an idea of what he values most, or what his dreams may be.

9. “Unlimited love or money?”

This can be a tricky question to ask because there’s a good chance he’ll pick love just to impress you. Nevertheless, his answer will give you an idea of what he values more – love or money.

10. “What’s the most embarrassing thing that happened to you as a kid?”

Asking this question will allow him to open up and share some of his life experiences with you. He will appreciate you having interest in his life and his childhood.

11. “If you could have dinner with one dead person, who would it be?”

This is an interesting question because the person he chooses is obviously someone he values very much or looks up to.

12. “Who is your hero?”

This is a question that will help you get to know him better and find out who he looks up to. The person (or character) he chooses will tell you a lot about his personality.

13. “What’s your deepest fear?”

This is a question that you may not want to ask on a first date, but it’s one that will help you feel closer to each other.

14. “What was your worst dating experience?”

Finding out what his idea of a nightmare date is can be useful, and his answer will help you get to know his dating personality.

15. “Before you call someone, do you rehearse what you’re going to say? Why?”

This is a fun question to ask, and he may even get a little embarrassed by it. If he’s the type to rehearse what he’s going to say, he lacks some self-confidence, or he may just want to make sure that he says the right thing. Either way, this is a great question to start up a conversation.

16. “If a crystal ball could tell you the truth about anything, what would you want to know?”

This is a revealing question because it gives you some insight into what answers he’s looking for in life. What he chooses is obviously something that is very important to him.

17. “How close is your family?”

If the two of you are getting serious, asking him about his relationship with his family will give you some insight into how much he values family. His answer will help you gauge whether or not his value on family is in line with yours.

18. “What is your most treasured memory?”

He’ll love sharing a positive, memorable story with you and appreciate you showing interest in his life. This is a question that will help you get to know him, but make sure that you follow up by sharing your own personal treasured memory as well.

19. “What’s your biggest pet peeve?”

It’s good to know what traits or habits annoy him. Hopefully, you’re not guilty of whatever peeve he may have.

20. “What’s on your “dealbreaker” list?”

What personality trait, behavior or action is a complete “dealbreaker” for him? His answer will let you know whether or not he’s easy going, or hard to please.

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