Ten Questions to Ask on a Date if You Want to Get to Know Him Quickly

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10 Questions to Ask on a Date if you want to get to know him quickly 

Feel Like a Muse (even if your guy isn't a poet)

Have you ever fallen for someone based on some superficial qualities, just to realize that you two have nothing in coming when it's a bit too late? Wouldn't it be nice if you could get to know him deep down a little sooner, so you don't fall for him before knowing that you are right for each other? I'll give you these ten questions to ask on a date, so you can get to know his true values and priorities.

Besides, these questions are fun and they will help your date to go smoother. You can use some of them during your video conversations before you ever meet him in person.Have you ever fallen for someone based on some superficial qualities, just to realize that you two have nothing in coming when it's a bit too late? Wouldn't it be nice if you could get to know him deep down a little sooner, so you don't fall for him before knowing that you are right for each other? I'll give you these ten questions to ask on a date, so you can get to know his true values and priorities.

Besides, these questions are fun and they will help your date to go smoother. You can use some of them during your video conversations before you ever meet him in person.


How do you know he is right for you?

If you are familiar with my advice, you would know that I emphasize the importance of monitoring your feelings and discerning how he makes you feel. This, of course, takes some practice and mindfulness. Self-Love Revolution: Express Your Feelings and Capture His Heart course can help you be more mindful of your emotions.

I chose these ten questions to ask on a date to help you see how he handles different situations in life and to see how his values align with yours.

They will also help you see how your relationship is going. You don't have to use all of them, and you don't have to ask them in any order. I don't recommend asking all of them in one sitting. You need to make that decision and ask when appropriate.

If he is the right man for you, he will feel comfortable with you because you will be more authentic and relaxed. 

Understand His Values

1. What’s the first thing you would do if you won the lottery?

This is a significant question. It will help you see where his heart is. A lot of the things we do in life are constrained by money, or the lack of it. Many people do a specific job because of the money.

But what if money wasn’t an issue? What would he be doing? Where would he live?

This is a very telling question to ask because it reveals our true values and what we really care about in life. If we win the lottery and we are no longer held back by money, we are free to do whatever we want.

We can travel, do charity work, and buy whatever our hearts desire. This is definitely one of the questions to ask on a date to determine his deepest desires in life.

2. Do you think everything happens for a reason?

Wanna have an interesting philosophical conversation? Then, definitely this is one of the questions to ask on a date. Here is another important tip when choosing a partner. Don't look for superficial nominal characteristics to check off when figuring out if he is right for you.

As I already stated, you should see how he makes you feel. Instead of saying, "Oh he is a doctor. We are intellectually compatible," determine if you enjoy stimulating conversations with him. I've met some highly educated people who are philosophically incompatible with me.

People typically either believe in destiny, that everything happens for a reason, or they believe in chance, that everything that happens is random and there is no real rhyme or reason. This is a very thought-provoking question that is sure to lead to an interesting conversation. 

You will definitely be able to see how he reasons. Is his thinking more concrete or more abstract and nuanced? Does he rely on empirical data or he enjoys speculative theorizing?

Most importantly, do you find him intellectually stimulating or not?

3. If you could relive any year of your life, which one would it be?

Another great question that will tell you a lot about his values. This questions usually goes one of two ways. Your partner will either want to go back and relive an amazing year of his life all over again, or he’ll want to go back and fix a year that wasn’t so great. Either way, the answers to this question are always enlightening. 

4. What advice would you give your younger self? 

This question can get surprisingly personal although it's not so intrusive. It usually ends up being a mixture of sad and sweet. Who wouldn’t jump at the opportunity to impart wisdom on our younger selves? This is also a great way to open up conversation about your childhood.

It will also help you understand how his values developed overtime, and what his priorities my be as he matures.

5. Which do you prefer, a good book or a night out?

This question reveals a lot about your partner's personality type. Introverts will almost always pick the good book, and extroverts will typically want a night out. This will also determine how compatible you are with your partner. Issues may arise if you want to stay home and read when he always wants to party. 

Questions that Will Help You Get to Know His Emotions

If you want a happy relationship, you need to find an emotionally mature, open, and compatible partner. How would you know this? Well, I will provide you with a few questions that will help you determine this.

You can determine if he is open or guarded. You can also get to know his ways of managing difficult situations and so on. These are all potentials, and you need to be aware that it is possible that your date doesn't open up until you two are closer or in a relationship. So, don't jump to conclusions.

Following are some questions to ask on a date to determine his emotional world.

6. What is your biggest regret? 

Are you interested in figuring out his deepest secrets and his emotional maturity? This can be one of the great questions to ask on a date. Of course, he may not be forward with answering, but it can also be understandable depending on the relationship stage.

Depending on how he answers you can determine how emotionally close he wants to be. For instance, he may respond stating, "My biggest regret is that I didn't invest into realestate when the prices were down," or he may share something more personal.

These answers will give you a glimpse into his emotional world, and it will help you determine how emotionally open he is.


7. If you were suddenly invincible, what’s the first thing you would do?

You want to figure out where his fears lie? This question basically removes fear from the equation and lets us do anything we can think of.

Would he go sky-diving or create a social media video post talking about all his political views? Asking this question can tell you a lot about his views, fears, and his dreams.

8. What is one thing that is absolutely unforgivable? 

By asking this question, you are giving him an opportunity to go back in the past negative experiences. You may learn what his limits are and how he handles pain in life.

If he's been hurt by a previous partner’s cheating, he may reveal this. You will also be able to judge how forgiving he is.

9. When is the last time you cried?


Some people won’t want to answer this one. They either won’t want to admit to crying, or they won’t want to talk about what made them cry. This one can be tough, but if you allow yourselves to open up and talk about it, amazing things can happen.

Note that you need to feel a bit more comfortable with him before you ask some deeply intimate questions.

10. What’s something you never want to do again? 

This question usually tells us about some of the hardest times in his life. If he decides to talk about it, it shows you that he feels safe to open up to you.

These times are usually the most transformative, so the answer can allow you to see what has made them into the person they are today. It also gives you the opportunity to admire his strength and transformations.

What's next?

These are only some ideas. You don't have to ask all of them. Likewise, you can ask different questions that suit you more in any given situation.

A word of warning. Don't make conclusions just based on his answers. As I already mentioned, you need to be aware of the stage of your relationship and his personality. Naturally, some people may not open up right away, but they may be great in a long-term relationship.

What matters is that you follow the guide of your feelings that tell you how he makes you feel. In order to do it successfully, you need to know how to distinguish your old pain from what he brings up. To do this successfully, you need to know how to process your emotions and how to communicate and ask questions that will help you clarify where he comes from.

Communicating like this helps you build a relationship with him if he is the right man for you. Don't miss out on getting the Self-Love Revolution: Express Your Feelings Capture His Heart course.

If you are looking to create magical attraction with an amazing man, you need to know how to express your feelings and needs. Your feelings are the path to his heart. 

Learn how to process and express your emotions. I created a course just for that. Self-Love Revolution-Express Your Feelings and Capture His Heart  course will help you learn how to communicate with your partner in the ways that will deepen your bond.

Learn how to express your needs and boundaries in the ways that will make your partner feel empowered to make you happy and protect you instead of making him defensive. Your anger is the key to your deeper emotions. Once you become aware of them, you can communicate much more effectively.

Learn How to Understand Your Emotions and  Communicate Your Needs 

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I offer online relationship coaching for singles and those in a relationship. Check out how relationship coaching can help you in your particular situation.

Let's see what you need to work on to have a happy relationship. Schedule a free disovery session with me, and we can discuss how we can work together. 

In case that you are not ready for coaching or therapy, you can sign up for my free academy where you can find courses that will help you with your love life. Sign up now to deal with your limiting beliefs that may prevent you from getting the love you want.

Get exclusive access to my best tips about love, dating, and relationships in the free Academy Resource Hub and download The Accidental Singledom Checklist: Are You Standing in Your Own Way?

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Online dating can be a great way to find the right partner. It's just one of the tools, but so many people struggle because they don't know how to utilize it properly if they are looking for love.

In this interview, Jerica Jack, love coach, gives us some great tips on how to avoid overwhelm and frustration with online dating.

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About the Author

I'm dedicated to guiding women from feeling confused and frustrated to feeling competent and joyful when it comes to matters of love and romance.

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