If there is a certain guy that you really like, you will definitely want to think about asking them certain questions. These questions can help bring you closer with him in a very big way. They can also give you a better idea as to whether or not he likes you back. This is one of the best ways to increase your intimacy with a crush.

1. What Goals do You Currently Have for Yourself?
It is important that you know what goals he has for himself, because it says a lot about him as a person. The last thing you want to do is to date someone who is aimless and doesn’t have a plan for their life. This will help you get to know him better as well.

2. What Was Your Childhood Like?
It’s also a good idea to ask the guy you like what kind of childhood he had. This can provide you with valuable insight into the person he is now. Everyone has a unique experiencing growing up, and it’s important that you know about his.

3. When do You Feel Most Insecure?
This is a question that requires him to be vulnerable. A lot of guys aren’t very good at this, but he will at least try if he really likes you. It creates a sense of deep bonding that will help to solidify your connection with each other.

4. How do You Approach a First Date?
This is kind of a vague question, which is actually a good thing. It will force him to really think and give you an interesting answer. If you want to know more about him, this is an excellent thing to ask.

5. What Do You Find Most Attractive in a Woman?
The answer he gives to this question will most likely reveal if he is really interested in you. Think about whether or not you seem to match the description he gives. If so, there is a very good chance that you will end up together.

6. What do You Expect of Yourself?
The expectations we have for ourselves are very important when it comes to our overall character. The way he answers this question will teach you a lot about what kind of person he truly is. You will find out what standards he holds himself to.

7. What is Your Dream Job?
When you find out a guy’s dream job, you can learn quite a bit about him. It might be something that is unrealistic, but it will still tell you something important. The answer to this question will ultimately be a reflection of the person he is.

8. What do you Expect of Your Romantic Partner?
It’s also important that you know what he expects from his partner in a romantic relationship. If you end up with him, this information is beyond useful. It will tell you what he is going to expect of you.

9. What is the Worst Thing You’ve Ever Done?
Most people won’t answer this question honestly, but you can always hope. Even if he doesn’t give you the whole truth, his answer will still say something about him.

10. Where Would You live if Money Wasn’t an Issue?
The place that a person chooses to live if they are given the option can tell you something about them. It might seem like a superficial question, but it can be quite revealing.

11. What is Your Idea of Romance?
Not every guy has the same idea of what is considered romance or romantic. This is something that you definitely want to know upfront.

12. What are your Top Priorities in Life?
When you learn about his priorities, you will essentially learn what he values most in life.

13. What is Your Idea of Relaxing?
Everyone needs a way to relax and unwind from the stresses of everyday life. Find out how he does this so you can get closer with him.

14. What do you Like Most About Your Life Right Now?
Find out if he is the kind of guy who really appreciates what he has by asking this question. You might be surprised how much you can learn.

15. What is one of your Biggest Weaknesses?
This question will let you know how open he is to self criticism and reflection. You only want to be with a guy who can admit he isn’t perfect.

16. What Are You Most Passionate About?
Every woman wants to find a man who is passionate. This question will help you understand what he feels the strongest about in life, which is very important. It will also show you where his priorities lie.

17. What is Your Favorite Thing About Being in a Relationship?
When you find out what he likes most about being in a relationship, you will learn something very important. The way he answers this question will tell you what he really values in a relationship.

18. What is One Thing Nobody Knows About You?
If he is even willing to answer this question, it is a very good sign. This is a big thing to tell someone, so it’s not to be taken lightly. It most likely means that he likes and trusts you. It requires vulnerability, which is something that a lot of men don’t do very well.

19. What is an Important Life Lesson You Have Learned?
We all learn lessons from our experiences in life, sometimes the hard way. Find out what your next potential mate has learned so far. This will give you a better sense of how he deals with failure and adversity.

20. What is Something That Always Comforts You?
It is a good idea to find out what gives him the most comfort so you can help him feel good as much as possible. Everyone has their things that give them comfort, so you should make a point of asking him this question.


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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