You Are Probably Not Saying Hi to Enough People

Note: This essay might only apply to guys, but probably not. It is especially relevant in a downtown/college/work setting, as long as there’s not a plague going on. I plan on adding relevant links as I find them.

You should say hello to more people. Let’s face it – you don’t say hi to strangers enough. You probably don’t greet them enough online and you damn sure don’t greet them enough in person. I know this because I was frequently the new kid in school, I enjoy talking to strangers, and even still I spent a lot of my time in college walking to class thinking “It’s that dude from accounting, I only know that guy’s first name and that he wears a Chicago Cubs hat. Let’s do a curt nod if we have to and get to class.”

This is a dumb way to live.

At some point you met your best friend in the whole world. It was probably somewhat forced at the beginning, but now you are friends and don’t think at all about how awkward that first conversation was. Here’s how I met a few of my best friends, in no particular order:

  • I asked to sit at her lunch table and she said no because it was too crowded (it really was too crowded.) We’ve been dating for years.

  • I’d had my first glass of wine by accident at a party. I sat there on his couch asking about the “sour Sprite” I’d just had while he played Mario Super Sluggers with our mutual friends. We live a few blocks away, play tennis together, and hang out every few weeks.

  • He knocked on the door looking for my roommate at 7 AM after I’d been up until 2 AM doing homework. I answered the door in my pajamas thinking he was someone else that I recognized. He ended up being a great roommate the next year. We text every so often and when we see each other around town it’s a good day.

  • We were assigned roommates, but before we met in person I sent him a snap saying hi + a Harambe meme and he responded with a pic of his under-chin and the caption “More like KILLARY CLINTON.” We live far apart and still talk once every few days.

  • We knew each other as little kids, both moved, and didn’t talk for years. I emailed figuring he wouldn’t respond. He responded. This is now the “longest” friendship of my life, and I am excited to catch up.

And yet for some reason saying hi to someone from class on the sidewalk is a burden.


Everyone has reasons for not saying hi on the sidewalk. I enjoy a quiet stroll and don’t like spooking people out, so I usually don’t say hi past sunset, or when it’s just me and another person in passing, or when it’s a girl walking alone. This was at one point more than 60% of the people I could possibly meet for the first time in a day, now it is more than 95%. The probability of making friends like the ones above was already low, and it has dropped tremendously since graduating. And that’s just the good motives! That leaves out a million other worse reasons you might not say hi to people, which are probably the real ones. Unless you are in the middle of a task or would be late to something, it is worth it to say hello. The process is cheap and simple: Make good eye contact, smile and say something polite. Talk for as long as you please. People fret about the details but doing those four things enough times will make you a god.

The friend who woke me up at 7 AM had mastered this art. On our way to class one day I realized that he greeted most people we passed. They knew him by name from various classes, hangouts, etc. because he would say hello when given the chance. He made time for this in his schedule, leaving early to say hi and catch up with people he hadn’t seen. If someone talked a lot and he was in a rush he would quickly explain so and promise to talk later.

This had huge rewards. Everyone knew who he was. He had learned a lot of skills: Confidence, how to politely excuse himself (a big one), how to make small talk meaningful, all because he was willing to embrace the initial awkwardness of saying hi to an entire university, one person at a time. Eventually people started doing his work for him (including here.) He was given great introductions and his reputation for kindness preceded him, so people were eager to meet him. He also disproved a lot of miserly cop-outs for not saying hi: He had trusted friends, a girlfriend, and a perfectly functioning social life. He probably had the best social life, since he was welcome in every single clique. I repeat: He was welcomed in every single clique.

When I point out how powerful this ability is, and how easily it could be replicated, I hear two objections.

  • Fear. This is the only “good” objection, but just because the solution is hard does not make it any less simple. This is only conquered with practice, but you get to celebrate each victory.

  • Potential burdens – “I have enough friends”, “I don’t want to talk that much” or the defeatist “what would we talk about?” You are not obligated to make anyone your friend, don’t really need to talk about anything, and you don’t have to talk any more than you wish. People just enjoy being politely acknowledged in their communities and you probably would too.


I recommend an in-person greeting if you can get one, but I am increasingly a fan of greeting people online as well. With pretty much everything shut down, the likelihood of meeting people at the local church, library, or coffee shop has plummeted. Even if those places were open, I still think introducing yourself on the internet is worth your while.

Although sidewalk encounters are random, greeting someone online shows deliberate effort. This is a little less like running into strangers on the sidewalk and more like asking someone to chat over coffee. The stakes are a little higher and it’s more demanding than liking a tweet, but it’s a powerful tool.

Reaching out online means the person trying to make contact has at least a general topic to discuss. There is no “what do we talk about” - you’re responding to a post, it is simply assumed that your discussion will pertain to the post. Your greeting has to be more inviting than “Hi” but “Hi, I saw your post and was wondering if you would like to chat about ____?” likely works well for anyone with a small following. Maybe you get Kanye’s number on a good day, I will update the post if he answers. There’s the raised fear of being ignored or told no, but the rewards are a lot higher for both parties if things go well.

It is nice to be recognized by your neighbors for taking the same route to work. It feels way better to be recognized by people from across the globe who just wanted to say your post was interesting, or that you made their day better. The inspiration of a few kind words can get people to do crazy stuff. It gets people to edit drafts they let sit for months, say hello to more people on the sidewalk, cancel their video game sessions to hone a craft. The small price of a cold shoulder should not scare you off from making your introductions.

Either Way – Just Say Hi More

By saying hello to more people, you are encouraging yourself and others to be a little more polite, encouraging a little more public trust, and potentially startling one or two people. You can get that down to zero if you don’t approach anyone from behind/leave a few feet of distance/don’t send them their own address. The benefits surely outweigh the costs. A lot of internet writing focuses on the big stuff – how to be more productive, how to succeed at work, how to succeed romantically, how to conquer the world on a four-day week and still have time for shitposting in the groupchat. Consider this a reminder that the small stuff matters too, and that you are probably underestimating the benefits of small acts of friendliness.