I do think there are some decent observations in the beginning of this article that a lot of people take too long to realize.

1) There comes a time in most people's lives where making friends won't come without a lot of effort. You will have to go out of your way to create situations where you can get to know people.

2) Asking probing, slightly uncomfortable questions can lead to deeper friendships. If you're the type of person who doesn't feel comfortable digging into people's feelings, it's worth it to force it.

That being said, you need to treat your friends like they're unique people. You can't read questions off a script and expect them to feel good about it.

This makes sense if the author is a student at a school of any meaningful size in a popular major. But it doesn't make sense for adults struggling to make connections outside of school. Assuming you work in an office, would you serially go from desk to desk asking coworkers out to 1:1 lunches? I'm a member of over a hundred groups on Meetup and I manage to find in-person events maybe every couple of weeks or so. And I talk to maybe 1-2 people at each one: everyone else mostly brings coworkers and talks to them instead. When I go work on a laptop at a cafe, I try making some kind of conversation with someone who is also there alone, but that's also usually 1-2 people a week and that's a sentence or two back and forth, not even a conversation.

I get the sense that even lonely people looking for more chances to connect with others have few promising encounters with strangers and can't apply that "filter fast" mindset.

I work for myself and generally with my work I am not interacting with people on a daily basis. I also got divorced two years ago and since then, I've made a concerted effort to be more social and do a better job keeping up with friends. I've made quite a few new friends since then, and several that I see at least a few times a month.

My take-away from this article mainly was that making yourself vulnerable makes someone else willing to share too. It's valuable to get to know someone better. I don't think it has to be done in a scripted fashion. For me, the opportunities tend to present themselves organically.

I've had some deep conversations taking a ski lift up a mountain, walking around on the street knocking on doors during a campaign, waiting around to launch at a flying site and on a long drive in a car. You'll probably learn that you have a few shared interests with that person. When you do, it makes finding opportunities to get together and do stuff easy.

I disagree with the author on a lot, but this is not a bad idea, at least for people you work closely with. I probably wouldn't take them to a sit-down place 1:1 unless you're already comfortable with them but grabbing coffee or a fast-casual lunch that you take back to the office is a good idea

Your critique of point #2 is that a middle-aged adult has less opportunities for casual conversations with a stranger than a university student?

Maybe. Off the top of my head, here's a list of places a middle-aged adult can find casual conversations that may lead to friendships: gym, grocery shopping, volunteer work, hikes, walking in the park, sports, library, cafe, public events, bar, club, mall, in the checkout line at any store... I can go on. If you consider all these different avenues, you encounter 100+ strangers every day.

I'm a middle-aged adult that had no problem making friends throughout school. It was easy, almost the default. I lost most of them to time and distance. And now, I find myself with little to no close friends, outside of my family and significant other, because making friends isn't the default as an adult. Making friends takes work!

The author correctly highlights that you must exercise intent to make friends. I've discovered some parts of this through trial-and-error over the past couple months as I've been intentionally putting myself out there, and have received promising results so far. I still have a ways to go.

I leave you with a recent experience of mine that touches upon a lot of the author's points.

I workout 5-6 days a week at the gym. Headphones in, don't bother me. I see this same guy every day I'm there. He's working out, but he's talking with people too. Half the people there know him. For weeks, we'd pass by each other and say nothing. Until one day, I passed him in the hallway and asked him "How often do you work out and for how long?" Such a random question, but I was curious because I see him every time I'm there no matter the time. He gave me a long detailed rundown, told me about his 165-day streak, why he does it, etc etc. We exchanged names and then went about our days. Since then, we've spoken to each other every time we see each other, and our conversations have gradually gone deeper and deeper. And there's something strange about him... he's present. He's not in a rush, he's fully engaged in the conversation, and he's not afraid to talk about anything. So when we talked about what we did for Thanksgiving, I shared a little bit of vulnerability about how most of my family and friends are spread out across the country in different locations. Well, he was familiar with one of them, and actually traveled there to propose and get engaged. Turns out we'd been to some of the same places off the beaten path and enjoy the same things. Then the next time we talked, I asked about his wedding, and he shared some vulnerability about how the woman left a year after the engagement, just before the wedding, so on and so on.

This experience isn't unique. Since becoming intentional, open, and willing to share my actual self, I've had this same experience many times over the past couple months. Once with the cashier who was checking me out at a sporting goods store. Our conversation twisted and turned into her sharing vulnerability about growing older, with her birthday just a week away. Now, when I see her, we have real meaningful conversations without feeling like we have to be "normal".

Yet still, after these positive experiences, I don't exchange information, follow up, or take initiative. And that's what I need to improve upon. Because why wouldn't I do that after having a few good conversations? Well because I'm scared, I don't want to feel like I'm imposing, and what happens if we don't actually get along. Oh well... just have to dive in. :)

There are definitely gym regulars (the guy wearing Top Gun shades indoors who uses 14 plates for his leg press and never puts them back). The extent of my socializing at that gym, over the course of two years, has been "sorry, are you still using that."

You can talk to anyone, not just the regulars, with a little bit of observation. Most people are happy to talk about their lives because we all go through life with little to no people showing an interest, not even people close to us.

Another example from just the other night, I see a person with an amazingly low percentage of body fat and muscle tone. That's a feat that takes dedication! So, I ask them if they strength train and run... how are you able to stay healthy without injuring yourself with that training volume... oh you run trails, do you have any good recommendations for someone just starting out (because I want to get into trail running), so on and so forth.

There's a wealth of opportunities for conversation out there my friend. Be proactive, give it a go!