When there is a certain guy that you really like, asking each other questions is a good means of bonding. The way he answers each question can tell you a lot of important things about his overall character. The more you get to know him, the easier it will be to decide whether or not you are really compatible. We have listed twenty of the best questions to ask a guy you like, and they are worth taking a close look at.

1. What is one of Your Favorite Hobbies?
Everyone needs some sort of hobby, and what we choose to do in our free time says a lot about us. This question will give you a good idea about the kind of person he is.

2. Is Family Important to You?
Some people place more emphasis and importance on family than others. This is something that you will want to find out early on. You probably want to date someone who thinks family is important, even if they don’t always get along with theirs.

3. Who Do You Consider a Very Interesting Person?
The answer that he gives to this question can also say quite a bit about him as a person. The people we find the most fascinating are a reflection of ourselves. His answer might just surprise you.

4. What is One Flaw of Yours That You Are Working on?
It is important for us to acknowledge our flaws and to actively work on them. If he does both, it is definitely a good sign. You don’t want to get involved with someone who isn’t self aware.

5. What is Your Favorite Part About the First Date?
The way he answers this question will give you some idea as to just how romantic he is. Everyone has a different answer, and you can get to know him a lot better by hearing his.

6. What’s One Thing That is Still On Your Bucket List?
We all have a “bucket list” of things we want to do before we die. This will give you a little bit more insight into the kind of person your crush is.

7. What is One of Your Strongest Traits?
Whether it loyalty, determination or something else, you’ll want to learn about some of his best attributes. The answer to this question will also tell you how he sees himself, which is very useful.

8. When is the Last Time You Took a Chance on Something or Someone?
Taking chances or risks is just a part of living, but some people are more calculated than others. The kinds of risks he is willing to take will say something about him as a person.

9. What is a Strange Habit You Have?
Ask the guy you like to tell you about an odd habit he has. This will give you an insight into what makes him unique.

10. How do you Make the World a Better Place?
We should all make an effort to make the world a little bit better in some way. Learning this will let you know what he does for this part.

11. How do you Deal with Stress?
The way that each of us deals with stress says something important about who we are as individuals. You want to date someone who deals with stress in a healthy and effective way.

12. What do you and your friends like to do together?
Find out how he likes to spend time with his friends and you will learn a great deal about him. If you are going to be in a relationship, this will certainly be important information to have.

13. Are You a Superstitious Person?
Some people are more superstitious than others, and his answer could be very interesting. This is the kind of stuff that makes people fun and unique.

14. How Would You Describe Your Sense of Humor?
His sense of humor is another very important thing that you will want to know about. It will help you determine just how compatible you are.

15. Choose One Word to Describe me
This question will give you some insight into how he sees you, and therefore how to proceed with the whole dating thing. Does he see you as more of a friend or potentially more? His answer should be quite revealing.

16. What three things do you Value More Than Anything?
Knowing about his values is also going to be absolutely crucial if he is someone you could see yourself dating. You don’t want to get involved with anyone before you know this.

17. If you were told you had a week to live, how would you spend it?
The choices that we make in the face of death can reveal a lot about ourselves. It might seem like kind of a silly question to ask, but it can be useful. This will help you find out what sort of a person he is deep down.

18. Have You Ever Stolen Anything?
This question isn’t so much about the answer he gives as it is about honesty. Is he willing to admit to you that he has stolen something in the past? This is the kind of question that not everyone is willing to answer truthfully.

19. What Instantly Makes You Lose Respect for Someone?
His answer to this question will tell you something about his morals and values. It might also give you a better idea as to whether or not you really want to date him. When you know what makes him lose respect for someone, you’ll also learn what he respects.

20. What is one of the best Decisions You’ve Ever Made?
The ability to make good decisions is not something that everyone has been blessed with. This question will give him the opportunity to do a little bragging while teaching you something new about his character. It will also let you know what he considers a good decision.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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