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5 Essential Questions to Ask on Your First Date

Dating is about gathering data in order to assess if you and the person you are going out with are compatible for the type of relationship you want to create. There might be sexual attraction between you two, however there also needs to be a match on character level if you want a romantic partnership to be successful.

The first date is not necessarily for creating connection, it’s more for evaluating if the person in front of you is worth your time and energy that would be required to keep dating them.

Ask the questions, listen to what they say and to what they don’t say, by this I mean observe their body language and their emotional state.

PRO TIP: You can get to know a person easier and faster by ‘reading between the lines’ and observing their behavior, than by listening to their words.

1. Are you a dog person or a cat person?

Why would you want to ask this silly question? Because you want to break the ice and create a relaxed atmosphere between you two. Although you are evaluating the other person, this doesn't mean you shouldn't have fun. Actually, feeling good and laid-back around someone is a good sign.

Also, asking this type of question is a great way to find out more things about them:

- Are you a dog or a cat person?

- I would say I am a dog person.

- What do you like about dogs?

- They are friendly, trustworthy, they are always there for you and you can have fun with them. (what they say about their favorite animal they may also think about themselves)

You can use any fun question to break the ice, you don't need to prepare yourself for this. Just stay present and curious about them.

2. What is the most embarrassing thing that has happened to you?

You can’t go through life with someone who doesn’t have a good sense of humor.

Most of us have been through embarrassing situations, whether in our childhood or in our adulthood. By asking this question you want to see how this person deals with stressful situations and how emotionally healed they are. If they start telling you the story of when they peed their pants in 3rd grade and the whole class laughed at them and they get really sad or angry, there is still an unhealed child in them who will show up further down the road.

If they tell you an embarrassing story and they seem neutral or they can even make fun of that situation, this shows they have either healed it, or they haven't been that affected by it in the first place.

3. What is your opinion on (insert a controversial topic)?

This can be anything from global warming, to Covid. By asking them this you want to see how they think and how they can back up their opinion. Can they give logical argumentation or are they just emotional about that topic (most people display anger when they discuss controversial topics)?

The goal in not necessarily for you two to be on the same page, but to see if they can critically think, accept someone else's reasoning and have an exchange of ideas with you, not just state their opinion and shut you down because you might have another perspective.

4. What is one thing you would never do?

How many times have you heard people “I will never …” and after a while they did exactly that thing? Actually, this may be something that you might have done yourself, I know I did.

When people state so adamantly that they would never do something, they will most likely do it. Why? Because there is a part of themselves which they have disowned and souls want to be complete, so God/Universe/Source will create an opportunity for their soul to become whole again and this will happen by unconsciously entering a situation about which they said they will never be in.

So, if the person says things like: “I would never cheat”, “I would never hit someone”, “I would never lie” and they also display a strong feeling like anger or outrage, there is a high probably that they will do that.

On the other hand, if they answer something like “Never say never” or give you some strong argumentation while remaining emotionally neutral, they are less likely to do that.

5. What went wrong in your previous relationships?

Are they blaming their ex-es or are they capable of telling you at least 2-3 things they did wrong in the previous relationships?

This will show you how emotionally mature they are and if they can take responsibility for their own faults. You can't create a happy and fulfilling partnership with someone who can't own their shadows. We all have some bullshit to deal with, can they see their own?

For the things they say they did wrong, have they amended them or are they still having those issue? What have they done to grow and transform themselves?

If you are currently dating someone or if you want to start dating, use the questions in this article to see if the other person is a good candidate to becoming your partner. If you want more questions, you can download my free “Guide for Conscious Dating” where I listed 30 questions you can ask someone to assess if they are a good fit for you.

What are some questions you would ask on the first date? How would you test the other person's character?


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