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10 First Date Questions to Help Go Beyond the Surface

It's time we start asking the hard questions on the first date, so we aren't wasting time on a second!

It’s easy to assume that asking hypothetical questions or interrogating your dates about their simple likes and dislikes (favorite color, top 3 movies, occupation, etc) will get you closer to understanding the people you’re meeting on your journey to finding the ideal partner.

While that information is important for getting to know this person now, I believe it is best to focus on habits, common ideals, shared goals, and analyzing the level of stamina or understanding to persevere through any personal, situational, or relationship obstacles. Also, be aware that you’ll need to address whether you want someone that is your equal or challenges you.

Your personal taste tends to change as you experience life. Your habits, goals, and practices tend to grow and expand just as your expectations for relationships will.

These questions below will allow you to learn whether this person sitting in front of you has the qualities of a potential long term partner, another friend, or simply needs you to escort them respectfully back to the streets.

I was in my Carrie Bradshaw mood this week and went on a date to test out these questions. Not only did it get the conversation going, but it showed me that this person and I were not compatible. AT ALL! They were repulsed by the thought of animals and bugs (other than dogs), would never leave their hometown, had no relationship goals or hobbies, and couldn’t see themselves hosting their extended family for holidays or random weekends. I was able to effectively understand them in one date without feeling like I was interrogating them in a dark room.

*As you read through these questions, also think about how you would answer them!

1. What goals do you have in your platonic or intimate relationships in this time?

It is healthy to set goals in all areas of your life that you wish to expand on or improve. In order to do so, you need to start asking yourself (and the people you wish to share your time with) what they prioritize and compare that to your own priorities.

2. Are you spiritual or do you practice any religion(s)?

This question is important whether your have a spiritual belief system or not. For some people, their faith is what guides them through life. If you are a person practicing some form of spiritual discipline, the person you intend on interacting with in your daily life should either understand your ideals or give you space to make decisions in ways that may be inclusive of your spiritual needs. If you are someone that does not believe in a higher power, the person that you date or interact with on a daily basis should be able to respect your beliefs, or lack there of, and how you act or process life because of them.

3. What impresses you most about yourself ?

Their answer (and yours !) will give you insight into how this person views themselves and what they prioritize in terms of their health, social status, physical appearance, emotional wellness, intellect, etc.

4. How do you celebrate holidays and/or birthdays?

To some, holidays and birthdays are not just capitalistic ways to lure in profits. It can be a way to reconnect, recharge, or appreciate those that have held importance in their life. Getting a sense of their mindset around holidays and birthdays can give you clarity about their relationship to family, friends, capitalism (lmao), and themselves.

5. Do you enjoy the company of animals? children?

It is important to be on the same page about your comfortable proximity to animals and children. Some people are completely disgusted by the idea of being near children or animals, and to some people this proximity is what brings them true joy. This doesn’t have to be a dealbreaker, but needs to be addressed before challenges arise later in the relationship.

6. What is a hobby you are most excited about now?

This will give you insight about how your date spends their alone time and maybe what they would like to pursue if money wasn’t an option. Some hobbies can be shared and enjoyed by multiple people and could also clue you in on where to go for this potential second date.

7. Without regard for money and time, how would you spend your birthday?

During your birthday, the people you choose to spend time with, the places you want to go, the activities you partake in (especially when all expenses are paid) can be a great depiction of what you’re appreciative of in life. It’s also a great way to understand whether your date feels birthdays are wonderful milestones of life, another capitalistic money-grab, or a dreaded day marking the age of their perpetually dying cells and organs. It’s a great way to decide whether you’re sitting in front of (or are) an optimist, realist, or pessimist.

8. Where have you traveled and what destinations are on your bucket list?

As someone who enjoys getting to know the world, different cultures, languages, and perspectives to further explore and expand upon my own personal perspective, knowing that my partner appreciates and respects other cultures is important. I can’t tell you how many dates I’ve been on where the person made offensive jokes or mocked a language making me and others involved sooooo uncomfortable. I’ve also learned that traveling for pleasure and never leaving a resort versus experiential traveling can breed totally different worldviews that I love to hear about when meeting new people. Travel stories are so interesting and can be a great conversation starter with the right person.

9. What was the last book you read? What made you pick it up?

I know people say that you shouldn’t judge a book by its cover, but I am a firm believer in judging a reader by the library they keep. Some people never get out of their heads/ their original comfort zones and only choose books that will impress a house full of guests. I personally love to see that a person genuinely enjoys their library and expands on it for themselves.

10. What do you do to stay active?

Last but not least, as someone who enjoys challenging their body and getting active, I want a partner that can keep up with me. I love lounging on a sofa or a good snuggle in bed, but I can’t go a weekend without a new hiking adventure and I enjoy traveling to find them too. It would be a much sweeter escape if my partner could join me! This question could mean the opposite for you, but it's just another way to gauge the habits of your date and act accordingly.

I know that I want to date someone that would enjoy my spontaneous adventures, eclectic family (including my animals lmao), the world's cultural diversity, etc. Using these questions, I found out quickly that this particular person was simply the type to enjoy life from the comfort of their home, alone. So back to the drawing board I go, not upset about time wasted but excited for a better match! I hope these questions can give you the same results (or better).

Comment your favorite question from the list below and let me know which ones you try from the list above!

</3 Osh

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Courtney Tousana
Courtney Tousana
Aug 31, 2023

I love it, I will def be sending this blog post to a few friends 😭

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