“The Limits of Friendship” is primarily about the Dunbar number, and the article’s attendant Hacker News discussion evolved or devolved toward discussing friendship more generally (“Reading the comments, I’d say many members of HN should probably invest more time fostering friendships”). Both remind me of discussions with friends, about the nature of friendship, and how most people seem ill-prepared for social life after school.

In American and perhaps Western society as a whole like-minded people at similar life stages continuously mix together from age five up to at least age 18 and often well into the 20s through school. Then people often stop routinely mixing with new people, different people find themselves in different stages of life, and the friend machine often stops.* Yet it doesn’t have to, but making friends and meeting people becomes a skill more than a side effect of being.

A friend observed that I have a “gift” for talking to strangers, which would probably be a funny observation to my family or people who knew me in high school. Still I thought the comment was awesome because I’m quite the opposite: when I was a teenager I was pathologically shy for a lot of my life, and it’s taken a lot of effort to cultivate the ability to be social with strangers. I wrote to the friend that casually and regularly making friends is a learned behavior for me.

I used to never do it (flirting with women was also a learned behavior, as extensively and embarrassingly discussed here). Now that I do, however, I’ve noticed that people think I’m automatically good at it. A lot of things people now identify as characteristic Jake behaviors are really, really learned. I think that the temptation to see them as innate is attractive because it excuses us from doing the work necessary to cultivate and practice them.

I don’t want to be one of those people who hit 30 and are like, “Gee, I don’t have any friends anymore…” Part of the challenge comes from friendships being defined by time-of-life. Single people want to party and mingle with other single people. Couples (often) with couples, since single people can be threatening to relationship stability. Parents of young children rarely hit the bars at 10:00 p.m. on Thursday night.

Generalizations are obviously not universally applicable to all people all the time, but they exist for a reason. People with kids identify with other people with kids and so on. Parents talk about babysitting and their children’s shitting habits (I seriously hope to never do that). Your best friend at 20 might have nothing in common by 30 depending on when / where / how you evolve.

I see more and more lonely people who are like “Why am I lonely?!?” Let me be harsh for a moment and say they’re like fat people who are like, “Why am I fat?” and “I want to lose weight.” Some people have medical or medication issues, but for most the answers are straightforward: “Stop eating cookies and drinking soda and do some pushups and ride your bike instead of driving your car.” The response is usually, “I don’t have time blah blah blah.” Problems have solutions and there are many ways to falsely divide people into two groups, and one of those ways is between people who do the shit necessary to be effective and the ones who don’t.

Everything I have learned I feel like I have learned the hard way, through enormous amounts of error. That’s one reason I’m not too pissed about being told I’m a novice lifter at the gym. Chances are the trainer is right and I need to practice. Practice is everything. I suck at everything until I try, really hard and really repeatedly, to get better at it.

Friendship also isn’t quantifiable, which probably dissuades some high achievers who want everything measured in grades, dollars, or some other metric (that Facebook can be measured in this way may be one problem with it). There are still guides to becoming better at people. For example, How to Win Friends and Influence People is surprisingly good. I heard about it through reputation and assumed it would be stupid. I was wrong. Read it, annotate it, read it again in three months. There is a reason it has endured for (literally) generations—I think it first came out in the 1920s or 1930s—and that’s because its advice is timeless.

“How to Be Polite” has one or two paragraphs that are brilliant (it also has some other paragraphs):

Here’s a polite person’s trick, one that has never failed me. I will share it with you because I like and respect you, and it is clear to me that you’ll know how to apply it wisely: When you are at a party and are thrust into conversation with someone, see how long you can hold off before talking about what they do for a living. And when that painful lull arrives, be the master of it. I have come to revel in that agonizing first pause, because I know that I can push a conversation through. Just ask the other person what they do, and right after they tell you, say: “Wow. That sounds hard.”

Because nearly everyone in the world believes their job to be difficult. I once went to a party and met a very beautiful woman whose job was to help celebrities wear Harry Winston jewelry. I could tell that she was disappointed to be introduced to this rumpled giant in an off-brand shirt, but when I told her that her job sounded difficult to me she brightened and spoke for 30 straight minutes about sapphires and Jessica Simpson. She kept touching me as she talked. I forgave her for that. I didn’t reveal a single detail about myself, including my name. Eventually someone pulled me back into the party. The celebrity jewelry coordinator smiled and grabbed my hand and said, “I like you!” She seemed so relieved to have unburdened herself. I counted it as a great accomplishment. Maybe a hundred times since I’ve said, “wow, that sounds hard” to a stranger, always to great effect. I stay home with my kids and have no life left to me, so take this party trick, my gift to you.

The resources are there. The challenge is implementation. Let me repeat myself: Making and keeping friends is a learned skill, which many of us never learn and some of us learn much later than we should.

* (Adolescence is hard because it scrambles all the rules and principles learn about friendship from approximately toddlerhood to say age 12. Tom Perrotta’s Election has a great line in which a character observes that sex habitually turns friends into strangers and strangers into friends. Francine Prose’s young adult novel Touch hits similar themes. It may be that many people are unhappy that we never really return to those pre-puberty rules and roles because our desires and incentives change, and we have powerful evolutionarily shaped drives to do certain things and behave in certain ways.)