conversations with friends
“Louis, I think this is the beginning of a beautiful friendship.”
Whenever I meet someone for the first time, I have two measures of determining the ‘success’ of that first encounter.
The first is whether I’m able to make them laugh. The second is whether I’m able to get them to make fun of me.
The first metric is quite common, and usually attainable without too much effort — of course, this may be an effect of subconscious pre-screening, where the friends I make tend to be the kind to tell jokes, and so naturally they are friends with other people who also laugh at the same kind of humor.
But the second metric is a bit odd. I’ve had friends question: why would anyone would like to be made fun of? and realistically, how do you even get someone to be willing to make fun of you on the first encounter?
The answer to the first question is easy — low self-esteem — but the answer to the second question is a bit more complicated.
I like to say that I wear my heart on my sleeve.
That is to say, I don't filter much from my life, and I don’t keep many secrets. I’m open with my failures, and even take the time to write 1000-word essays about them. Whenever I meet someone for the first time, it won’t take long for me to go into a tirade of stories ranging from light-hearted anecdotes to recollections of terrible dates.
But I realize that not everyone is as open. Not everyone is comfortable retelling some of their worst moments on their first, second, or even tenth encounter.
And so every conversation with a new person is always a bit of push and pull — it’s a tango of seeing how much you can understand about this person from one conversation, and seeing how much they can reveal about you.
I think everyone has their own yardstick for how much they’re willing to share and how much they’re willing to ask about someone. Everyone has their own level of how much they’re willing to understand, both about others and themselves.
So how do you find out where someone draws the line?
“What’s your childhood trauma?”
A question that I jokingly suggested to my manager at the time when we were thinking about questions we could ask during our team’s bonding time. Surprisingly, they ran with it, and at this point, I think they’ve asked that question to at least 40 people. It’s now also a question that I like to ask.
It’s a question that catches people off-guard. It’s a question that reveals a lot about who you are as a person. It’s also a question that most people would never ask on their first encounter.
But at this point in my 20s, I’ve started to ask more questions like this whenever I meet people for the first time.
I’m happy to do small talk, and I find that learning to do small talk is an increasingly important skill as you grow older. But if I had the choice, I would always choose conversations that peel at someone’s layers, that gives a glimpse of what they’re like when they’re not posturing on social media. I’d like to learn about their trauma, their failures, who broke their heart (and who mended it), what makes them tick, the weird obsessions they may have.
And so questions like “What’s your childhood trauma?” are questions that I like to slip into the conversation every now and then when I’m meeting someone new. It has varying results of course — some people aren’t quite keen to share trauma to a person who is essentially stranger-adjacent. I’ve learned to not push when some doors won’t open.
But for some other people, the question opens a floodgate, where they share a story that gives a glimpse into why they are the person they are today. Of course, as with any first encounter, there are some things that people will tiptoe around or be reluctant to reveal. But the ice is broken, and the conversation afterward will be much more open than it would have been if the questions had remained at surface level.
However, the real purpose of the question is not to hear a story about what traumatic experience they went through as a child (although that’s interesting in its own way). It’s to understand where they draw the line in conversations with friends — and where I can push it.
There’s an excerpt from an article from Nix:
Deep down, I think we all know what compatibility feels like because we’ve felt it before in at least one arena of life. It might be work or platonic friendships or hobbies. It is that click of pure recognition. It feels… natural. Instinctual, almost.
It’s rare to find someone who clicks with you naturally. Someone who just understands your jokes, who has the same level of emotional depth as you do, who likes the ideas you like. I can count the number of times it’s happened to me on one hand.
But I don’t think compatibility is solely based on clicking naturally with someone. I don’t think that you should only be able to be compatible with those who are already naturally at your level.
Rather, the way that I’ve found best works to see if someone could be compatible, especially on a first encounter, is to match their level. Instead of asking them to come to my level, I meet them where they’re at instead.
Jarring questions like those about childhood trauma are good to find out someone’s boundaries — if they are reluctant to answer, I don’t push, and I find other topics that they would be comfortable with. If they answer, I ask more, and see where they start drawing the line.
See, the real reason why someone new making fun of me is interesting to me is that it’s a sign of comfort. You don’t tend to make fun of people you’ve just met. But if they make a quick humorous jab at me, it’s a sign that I’m doing something right with the conversation, and meeting someone at their level.
Just the ability for them to make a joke about me signals two things for me: (1) that I’m being open enough that they know more about me than most people would typically share and (2) that they’re comfortable enough to poke fun at me as if I’m a friend they’ve known for a while.
Nevertheless, comfort does not necessarily mean compatibility. It does not mean that I will become life long friends with this person, nor may I ever see them again after this first encounter.
But I try to make people feel comfortable anyway.
This is just something that I’ve spent a lot of time thinking about throughout my various conversations with friends, new and old. Take this writing with a grain of salt, as I am a people pleaser by nature and also an overly keen extrovert. I understand that this takes effort, and not everyone would like to take the time to match someone else’s energy.
But I find that taking that extra effort to meet someone at their level, especially for those who I find to be extremely interesting despite not instantly clicking, is very rewarding. It’s nice to find someone who you click with, but the majority of people that we’ll meet in our lifetime are not people that we’ll naturally be on the same level on.
I’ve understood that the people who will become my best friends are not always the people who I am instantly compatible with. I understand that some people take more time.
So I always try to make people feel comfortable first. I meet them where they are, and poke them a bit to see if they’ll poke back.
Sometimes they don’t and that’s okay. You can’t be friends with everyone.
But sometimes they do, and that can be the beginning to a beautiful friendship.
