Relationships 101

When we talk about privacy, we tend to think of technology: VPNs, messengers, metadata, and cameras. When we do think about relationships, we tend to think of them in terms of social engineering. But the fact is that most of us are not Elliot Alderson or Thomas Anderson. Most of us have jobs, hobbies, and an innate need for social interaction. Humans are social creatures, and while the amount of human connection we need varies from person to person, most of us still need it to lead an emotionally healthy and fulfilling life. Unfortunately, it seems that a number of people in the privacy community struggle to find connection once they’ve become passionate about privacy. To their defense, it’s not hard to see why. Our society has become increasingly digital: “Netflix and chill,” “add me on Facebook,” “Google it,” and more. Choosing to live a privacy-conscious life can be a one-way ticket to isolation if you let it. The good news is, it doesn’t have to be and you don’t have to let it. In this blog post, I want to talk about a few people skills and life hacks I’ve picked up along the way that have made my life socially fulfilling without compromising too much on my privacy goals. These skills can be applied to various levels to help you find love or simply be part of the workplace. This blog post can also work in conjunction with some other “people skills” posts I’ve made in the past, like “How I’ve Convinced People Around Me to Care About Privacy” and “Interacting With Non-Privacy People.” For some of you, you may have already mastered some or all of these skills. Congrats. But for those who struggle to find connection, read on.

Let’s start with the most obvious, basic things: if you’re not a likeable person, nobody’s going to want to connect with you. There are three skills I’ve found that can make a person likeable: sense of humor, breadth of knowledge, and diplomacy. I want it to be noted that I had virtually none of these skills growing up. I had to learn them all. These are not natural traits like height or skin color that you’re born with and can’t change. You can learn them if you put your mind to it.


Let’s talk about humor first, because in my experience this is where you get the most mileage. Humor consists primarily of subverting expectations. Consider the following joke:

Two farmers are talking to each other about their size of their land. One farmer brags “well I start driving the property before sun-up, right after breakfast. After driving for hours and hours, we pause for lunch, then keep driving. We just keep driving and driving til supper time, then we drive some more until the sun goes down.” The other farmer nods and goes “yup, I used to have a truck just like that.”

Now admittedly, this joke isn’t the funniest thing I’ve ever heard but I bet you that if you told it to most people they’d at least get a chuckle. That’s because humor is about breaking the tension with something unexpected and surprising. In this joke, the tension suddenly shifts from the incredible size of the farmer’s land to the poor quality of his truck. Consider this other joke: “there at 10 types of people in the world: those who understand binary and those who don’t.” The humor occurs when a person is expecting me to list off ten different types of people or personality traits, but instead I make it about a binary where there are only two options. The joke is further compounded by the fact that I clearly don’t understand Binary myself.

There are, of course, different types of humor. I thrive on sarcasm and dark humor. There’s also puns, stand-up, actual jokes with a setup and punchline, etc. There’s a million ways to tell jokes, but at the end of the day they all come down to a break of tension. This is why a lot of speakers start with a joke or funny story. It breaks the tension and makes everyone feel at home. The most important thing is to know your audience. Telling a dark joke in an HR meeting is probably not a good idea, and telling a tech joke to non-techies probably won’t go over well (my mom would not understand that binary joke to save her life). Not everybody is a master of every kind of humor. I couldn’t do stand-up comedy, but I am a master of situational humor. And not every joke is going to land. That doesn’t mean you aren’t a funny person, it could mean the people who heard it weren’t paying attention, didn’t get it, or aren’t in the right headspace for jokes. But if you can learn how to crack a well-timed joke tailored for the right audience, that’s a good way to get people to like you. This is probably the nerdiest thing I’ve ever said, but if you struggle to be funny I recommend “500 Clean Jokes and Humorous Stories: And How to Tell Them” by Russel and Linda Wright. I read this book as a child and it helped me understand why humor works and what makes people laugh.

Breadth of Knowledge

When I started high school, I was a hardcore gamer. I didn’t know anything about politics, I didn’t have a job, and I didn’t (and still don’t) like sports. If it didn’t concern X-Box, Gamecube, or PlayStation 2 then I didn’t care. While there’s nothing wrong with being a gamer, this made me incredibly difficult to talk to for anyone who wasn’t a gamer. I didn’t know any movies or TV shows, I had no additional hobbies. I really can’t stress how hard this made it for me to carry on a conversation with anyone that wasn’t about a video game. These days, I’m much more well-rounded. I’ve seen a wide variety of movies and TV shows (mostly scifi and horror), I’ve read classics like Dracula and Frankenstein as well as modern books like American Gods (as well as all of HP Lovecraft and Edgar Allan Poe). I read enough news to know what’s going on in the world broadly. This means that I can now carry on a functional conversation with almost anybody about almost anything, from current events to pop culture. No matter who I’m talking to, we can typically find something to talk about. Keep in mind, I never pretend to be an expert, but I know enough to talk and have an opinion.

A lot of people in privacy who struggle to make friends seem to lack this. They’ve fallen so far down the rabbit hole of privacy that that’s all they can talk about anymore. Don’t get me wrong: I can talk about privacy for hours – and admittedly I probably steer the conversation toward it more often than I should – but it’s far from the only thing I can talk about. If every time anyone mentions anything you inevitably tie it back to Big Tech and encryption, you may need to develop some other hobbies. Take up gaming, fitness, reading, psychology, cars, anything. If you want to connect with people on any kind of level and make them like you, you have to be able to talk about more than just a few niche topics. For this, I strongly recommend the podcast “Stuff You Should Know.” They lean left politically, for those who care, but they usually don’t cover political topics and they’ve been on the air for over a decade, so they’ve covered everything from grass (like the kind that grows in your front yard) to serial killers in deep, well-researched detail. This podcast should give you a great passing knowledge of a variety of topics. You don’t even have to listen to every episode, just pick whatever sounds mildly interesting.


Last but not least, let’s talk about diplomacy. Winston Churchill once famously described diplomacy as “the ability to tell someone to go to hell in such a way that they look forward to the trip.” In this case that’s probably not the message we want to share, but the point is that it’s the ability to delivery a message in an amicable way, even if it’s an unwelcome one. For example, earlier I mentioned that I’m not into sports. When I’m trying to connect with someone and they say something like “did you see the game this weekend?” I usually reply with something like “nah, I’m not really into sportsball, but my dad was a big Sooners fan growing up.” This serves two purposes. One, it injects some humor with the phrase “sportsball” (which a word that usually implies “I know absolutely nothing about sports of any kind, not even what they’re actually called”), and two, it tells them I’m probably from Oklahoma because the Sooners are a college team from University of Oklahoma. That naturally leads them to ask “oh, are you from Oklahoma?” and turn the topic toward where we grew up, which is something else we can talk about and find common ground over. Maybe they didn’t grow up there, but they might have visited. Or maybe they have a friend from there.

The lesson here is that diplomacy is subtle. It’s not an instant, hard shut down of communication (ex, “no I don’t do sports.” End of statement, end of conversation) nor is it some kind of awkward question dodge (ex “you see the game last week?” “Nope, so where are you from?”). It’s a natural flow to the conversation, directing it in the direction you want to go. It’s almost like social engineering, except the goal isn’t to extract any specific piece of information from a person, only more information that you can both share.


Throughout this article, I’ve used the term “connect” multiple times. That’s because it’s important to remember what the goal of communication ultimately is: connection. No matter the form of communication – film, text, or spoken word – the goal is to create a relationship with a person and transfer a message. Sometimes the message can be about society, sometimes it’s about trying to impart the importance of privacy, sometimes it’s trying to say “I’m someone you’d get along with and you should hang out with more often.” But unless you can find a way to relate to that person, that message won’t stick. And that’s really what communication and connection is all about: finding common ground. If you both like Italian food and cooking, that’s a connection. If you both like black-and-white horror films, that’s a connection. Finding and cultivating these connections is ultimately what will make people like you and want to spend more time around you, and fills that social need.

Privacy is important. Privacy is a human right. But it doesn’t have to mean being alone and isolated from the world. You can be private and still have friends, family, and fall in love. It just takes some practice. And the more you do it, the better you get. Assuming it’s safe to do so with the pandemic and all, getting out is the best way to practice and develop new connections. Figure out your interests, then figure out where those people gather: concerts, old movie screenings, EFF meetups, cooking classes, you name it. It just takes a little intentionality.

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