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  • Saskia Scarce


Updated: Apr 15, 2022

By: Saskia Scarce
“You are a good conversationalist”, says a person that I have known for years.

I smile instantly.

“You are such a good conversationalist!”, said a random person whom I had just met that day.

I instantly smiled. It was super refreshing because, recently, I’ve been trying hard to facilitate meaningful connections. The thing is, I have always loved talking; sometimes, you wouldn’t have been able to shut me up. Growing up, I was told frequently that I “talk too much”. As such, I began to view myself as a nuisance to others, even when that wasn’t necessarily the case.

However, I also found this skill to be super useful when in elementary and highschool, because it allowed me to make friends easily. Now, while attending University online, I find that my extroverted personality can be helpful in establishing/nurturing those social connections.

How this translates into my dating experiences — (Mom, Dad, you didn’t read that) — is super interesting. It begins normally; let’s say I am meeting someone for the first time. We talk about the general stuff: how’s school, what’re your hobbies, do you play any sports, ect. I HATE these questions. They are boring, and… blegh. I say this because it doesn’t reveal anything about their deeper essence and their upbringing, their values and quirks. To remedy that matter, I’ve started to ask unusual, unique questions intended to dig a bit deeper.

Here are some my favourite questions to ask:

What colour socks do you prefer to wear? Why?** Alternative question: white or black socks and why?

  1. What is your favourite fruit, and why?

(Sidenote: The two questions above can be seen as silly, but you can figure out a lot about the person. Are they a sneakerhead? Did they, perhaps, grow up with strict parents? Or did they grow up in a different culture?)

  1. What is the most sentimental gift you have ever received and why?*

*Alternative phrasing: ‘sentimental’ can be swapped out for ‘best’.

People tend to become super comfortable with you after questions like these, as there aren't any sort of expectations. There are no right or wrong answers. Conversations don’t feel forced, flowing naturally and organically instead. As you continue to talk more and confide about your friends, family, goals, aspirations, and fears, a foundation for a deeper emotional attachment is created.

Even outside of talking to people romantically, I form a lot of genuine connections with people and sometimes I envision how they may fit into my future. Now, in terms of romance, this is draining as hell.

Let me set the scene for you: let’s say you are talking to a person for a bit, pushing through the basic questions to reach the more meaningful ones, and you manage to form a bond. Then, suddenly, you guys stop talking for whatever reason. Now, there is another person out in the world that knows the little things about you: your dreams, your hobbies, and even your sock colour preference!!

I find that, specifically, to be the most difficult part of establishing connection through conversation, as it’s often so emotionally draining. After all, you gave sacred elements of yourself through these conversations, and you learned their truths in turn. You are left hoping those people are accomplishing their goals in spite of their fears, even though you no longer speak.

I know that is a dark concept, but even still, I think that talking and having conversations are an essential part of the human experience. You grow, you learn more about yourself; you leave an impression of yourself on the other person just as they did on you.

“You are a good conversationalist”, says a person that I have known for years.

I smile instantly.

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