On Conversation and Making Friends: Post-Grad Edition

Back in junior year of high school, I had a revelation one day that something just wasn’t right with the way I interacted with people. From that moment, I decided to embark on a little mental project to think about, observe, and research how people develop friendships, interact, and converse. The result was like night and day — did you know I used to think that extended periods of silence were fine when I was with people? Yeah. So I feel that I have some legitimacy on discussing this topic, though actually not really. It’s a complicated thing, and I’ve learned first and foremost that something that works with one person may not work with another. Ironically, applying experience gained with one person to another person is a common rookie move. Yet there are some shared themes here.

Before I move on, I would like to explain that head knowledge doesn’t necessarily translate to savvy, because knowledge is dead until applied. This is no more evident than the fact that I am ridiculously bad at making/maintaining friends and conversing, and I’ll be expanding on why this is so in my post as well.My post is getting too long.

Oh, and one final thing: the myriad of lessons I have learned can fill a book. I’ll limit myself to the major things I have taken from a half-year of post-grad life.


I still occasionally (okay, who am I kidding?! always…) analyze social interactions that I watch from a spectator standpoint. One such moment was when some neighbors invited my family to a Thanksgiving feast. Now the host of the party has had a life. He’s a white Caucasian American, and he’s married to the hostess, a Chinese lady who has a background not too dissimilar to my parents, and who has broken English and has not been in the US for long. Apparently, he’s been in China and Taiwan and the Philippines and Europe and just about everywhere, and he’s not hesitant to talk about his experiences. Two other (Chinese) guests were there, and the conversation flowed pretty well between them and the host despite the obvious language barriers. But whenever the host talked about his travels, my parents and I were silent. It was fun listening and vicariously living through his conversation, but there was simply nothing for us to add.

The difference: my parents have not lived the easiest life, and they’ve had no luxury to travel often (for instance, after they came to the US, they were not able to go back to their China homeland for 20 years). The other guests did.

In contrast, when we talked about work, even I had something to say.

So therein lies really the key to conversation, one which I had known well before, but the Thanksgiving dinner strongly reinforced:

Your conversation builds on your life experiences. If you don’t go out and experience anything, you can’t talk about anything.

And if you can’t talk about anything, well… a lot of people are going to find you boring, and it’s going to be harder to make friends.

On a final note, guess what my parents always talk about when I’m on the phone with them? That’s right, work/career/school — without much variation. Because those are the experiences that dominate both our lives.


A few months ago I became very confused, and a little bit envious, about why my female roommate always goes out and parties with friends, and why I am here struggling to maintain my current friendships and build new ones. She’s a few years older than us, a grad student at Berkeley, but surely that can’t explain all of it? So I finally summoned the courage to ask.

What followed was a rather insightful exchange. In summary,
a) She was kinda like us when she was our age
b) She really can’t live without a ton of social interaction keeping her going (a flag for an extroverted tendency much greater than my own)
c) She’s only close to a few people even though she interacts with a lot of them.

As for the takeaways:

If you want friends, you have to prioritize it and make the conscious, consistent effort and time to reach out to people. For some people it’s more important, so they will naturally prioritize it higher, make more effort, and thus make more friends. If it’s important for you, you have to go out and be proactive.

The failure to success ratio of making deep, lasting friendships is crap for everyone. But you never know who it’s gonna be.

The first few times are always awkward for everyone. It’s okay, and it may take a few dinners/hangouts to properly break the ice.

This differed markedly from my previous experiences. For one, you’re always in close proximity with friends in school, so a minimal amount of effort to develop friendships is sufficient. Such is not the case in real life. For my roommate, she absolutely needs social interaction. Hence she prioritizes it and the effort she has put into it has paid dividends.

Secondly, I always thought I was the most awkward man in the house when confronted with someone new. It’s really a fantastic relief to know that everyone goes through the same thing.


I feel like this post is going to be a highlight real for my interaction with my female roommate, because it’s certainly evolving that way. I’m going to backtrack and look at Day 1, to our first few meaningful conversations.

I reenact this scene often in my head because I realize it was a fatal mistake… and really, she doesn’t talk to me or my HS-friend-roommate often anymore partly because of this. Forgive me; I was still naive.

Anyway…. I was really, really excited to have this third roommate. I was coming off my lonely depressive episode, and I was eager to start off my recovery on the right foot by making a new friend from this new roommate. Hence, I wanted her to get to know me better. For my first conversation with her after she moved in (or somewhere near there, can’t remember), I went ahead and acted my usual nerdy self, talking about physics and just being totally wacky.

Her reaction? Not positive.

I think either consciously or subconsciously she realized I was not going to be a friend-candidate. Since then, she has actively resisted almost all attempts from me reaching out. Man, that’s a bummer.

Life had spoiled me. An abundance of fortune had fooled me into being overconfident about my abilities. I was lucky to find people as nerdy as me in school, who really bonded with me through this nerdiness. I was foolish and naive, and believed it could do in Real Life as well.

Actually, I was wrong on two fronts, only one of which was due to the incorrect extrapolation. Even my Berkeley friends, towards the end, grew tired of my nerdiness and stopped engaging me in conversation. That should have been my first red flag. But I was blind and I only saw this in retrospect.

It’s wrong to say that I can’t be nerdy. But it is right to say this:

Engage others in a way they enjoy to be engaged. And in particular, when initially getting to know someone, engage the other party in a way that is NOT freaky or extraordinary deviant from the mean. That’s right, it’s actually NOT cool to be weird in the beginning. Engage in a way that has a high probability of being received by the other party in a positive manner. When you get to know one another better, that is when you can slowly weave your weirder mannerisms into the interaction.


So there, three big sets of takeaways. Actually, it’s not even close to even all the lessons I’ve learned post-graduation. There are so many that cannot be covered in a 1300 word piece, so be on the lookout for a potential second post!


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