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Yes it's obviously beneficial. Alone you are just alone. A lot of people don't have many friends or just don't have time for them. Still it's difficult. I always worry about how much of a creep I am, so I don't do it very often.
You are not a creep. Nicola Tesla, Buddha, Neo from Matrix, Einstein where all alone, introverted and socially awkward :) I personally don’t like to derive my identity from the external world or how well strangers respond to me. I’m a lone wolf and love being alone
I’m not 100% sure what’s behind the feeling of “creeped-outness”, but my immediate intuition is that it has to do with a sense of possible threat from an unfamiliar person, ie “stranger danger”.

One way of reducing that is to connect through the current shared reality. Small talk is basically this sort of connection. For example, standing in line at the DMV, perhaps you notice the person behind you looks disengaged and bored as well. “At least this line is moving a little faster than I expected.” The person might respond with short chuckle, “Hah, yep.” Or they might expand on your thought, “Yeah, I was here last week and it was nuts.” That introduces an opportunity for further conversation, “Oh really? We’re they not able to help you that time?”, etc

Even if the person just answers with a short laugh or an even more basic eyebrow raise, that short interaction can increase your comfort, and help train your brain to find those moments for small talk.

The times I’ve ever been blown out by a stranger are when our energy levels vary wildly, ie they are hyped up and I’m sitting still, or vice versa, or they’re in a group of people, etc. Otherwise, people generally seem welcoming to that quick connection because of the increased comfort it can cause, even if the conversation itself is inconsequential or trivial.

Yep, I think you're dead on. Its interesting that the OP didn't want to have small talk with strangers because they're afraid of looking like a creep. The point of small talk with strangers in public is very much just to signal, "not a creep, just a regular person like you" and increase comfort levels. Unwillingness to engage or over-sharing usually send off the wrong signals, but simple quick, "Hey, crazy weather, huh?" conversations put people at ease.
I changed from extreme reluctance to engaging with strangers to the opposite, talking freely and easily to anyone, from age about 40.

It changed my life, for the richer.

It took a while to learn how.

Most of my learning was unlearning - how to not feel awkward; how to not sound inquisitorial, superior or annoying, how to not be frightening.

And some learning was constructive - how to talk about small stuff. I’d avoided that because I thought of myself as more consequential and intellectual than that, but I was wrong.

In fact, talking about that bus, or that billboard, or that dog’s haircut, or that man’s coat, is key. People respond by answering in kind - friendly, upbeat and curious. They can do this precisely because the topics aren’t personal or weighty, but there’s enough content in expressing a sentiment or a point of view for them to make a small personal statement.

Once a conversation with a stranger is started with the right energy, it’s as emotionally satisfying and meaningful as a casual conversation with a colleague or friend.

It's a shame we learn to appreciate talking to strangers only around the middle age. In ages when it would be the most useful and fruitful - 20s, early 30s many fall into the "no bullshit" attitude, feel rebelious superiority, socialize only within cliques. As a single man I might chat with women in their 40s and older but that's too late (for them) to create family with children.
Abandonment comes to mind. A lot of us is assumptions, leaving them aside makes from a more open minded experience.
Same here. I'm an introvert so it doesn't come naturally, but a good tactic is to talk about a joint "thing" that affects both you and the other person. In the UK this is usually the weather "do you think the rain will ever stop?" - but this is boring and I avoid talking about the weather. Another example might be "they used to employ more people here" if you are both waiting in a queue (line) at a shop. You have to be careful not to come across as moaning / complaining, because you don't want to be that guy :)
That sounds really powerful!

Can you share more? What did you learn? How did you overcome your fear of sounding awkward? What made the difference in not coming across inquisitorial or superior? What would you say was holding you back the most in the past? If you could go back in time and coach yourself, what would you do to change yourself within one week?

I think these benefits are probably less surprising for many people after lockdowns & social distancing almost completely removed such interactions from our daily lives. This is also something that those of us who work from home will miss out on some opportunities for.

Somewhat differently, I moved from a country where small talk was common, to a country where it's much less common (plus the working from home and I'm not comfortably fluent enough in the language) and I really miss small talk even though I'm an introvert. Exposure to humanity is indeed a good thing.

It's interesting how cultural norms vary around interactions with strangers. I'm British, so interactions with strangers are often limited to a reluctant "hi" if out walking at quiet times of the morning – yet when I went to the US, people would say hi in hotel elevators(!) and I had a random guy give me a quarter when he saw me struggling with change for a meter – things that had never happened to me in the UK. I think I learnt more about small talk over my numerous trips to the US than I ever did in decades of growing up in the UK, but it's benefitted me back here too, because really it's about initiating such interactions, not just stumbling into them.
It's curious to me that I've on a number of occasions seen UK folks make reference to the horrors of US folks saying hello in the elevator. Generally here in the US I don't see a lot of that. It's usually a dance of awkwardly looking around so as to not make eye contact and then have to acknowledge others in the elevator. More recently, cell phones make it easier to have something to stare at. Perhaps it is other parts of the US where folks typically chat in the elevator?

When I was in Tokyo last, I got in the elevator and there was one other guy in there with me. He asks me if I'm American and when I said yes, he grinned approvingly and enthusiastically said he, in fact, was South Korean. I was very confused as to why he thought that meant we had some kind of connection. He then asked if I wanted to come back to his room for a drink, which made me very uncomfortable because I just wasn't able to read the social cues well enough to understand his intentions. I politely said I was busy. I'm guessing he was just trying to be friendly, but I sorely wished I could just stare at my cell phone and not interact with him.

Could it be a California thing? I've spent perhaps 90% of my US based time there.

I was very confused as to why he thought that meant we had some kind of connection.

Both foreigners/travellers, perhaps?

Do you mind if I ask where you're from in the UK? I find that there's an awful lot of variation between different regions. For a few years now, I've lived and/or worked in London, where chatting to strangers is not the done thing. But travel to certain parts of the north of England, or Scotland or South Wales, and the norms are much more like what you describe in the US. My father was from South Wales and he loved visiting the States, where he found people to be open and friendly and willing to chat, just like they were where he grew up.
London for 20 years then "oop north" for 20 years, so I know what you mean. Talking to strangers is more natural up here for sure, although there is still a wall of "why is this person talking to me?" to break through at the start of any conversation. I think maybe the accent breaks through a lot of barriers in the US.
thoraya maronesy on YouTube has many videos around this theme. Strangers talking about deep thoughts, talking to random persons passing by (behind curtains)

Worth looking at a little

My friends call me hobo whisperer. It comes to me naturally.
This is so great for those who is afraid to go beyond their comfort zone! The social adaptation is one of the most important living skill, which affects one's quality of life. So by talking to strangers, you definitely gain experience, courage, social adaptation, creativity, your neural connections develop and fire, so so so many benefits!
I hadn't really talked to random strangers until I moved to a new city a few years ago.

I didn't know anyone and I felt a lack of connection so I moved out of my comfort zone. I ended up pursuing dancing and became a dance performer

After awhile I've met some really close friends who I treat like a 2nd family

It's made my life a lot richer and happier as a result

I struggled for the longest time because of my upbringing as a child. I was anti-social and submissive, mostly as a result from being raised in a traditional asian household. My dad and brother are both very non-emotional and have dominant personalities. My dad would always embarass me whenever he got the chance in front of strangers. My brother would always use my words against me in conversations and tattle-tale on me so I had a lot of trust issues too. One of my best friends describes my family gatherings as an "exchange of information"

I've been going on dates as a single guy right now and it's been kinda hard for me. Sometimes old habits kick in for the worst.

I envy people who had great childhoods, and anytime someone talks about how fun and great their upbringing is, or how close they are with their family, it sometimes makes me a little sad reflecting on my own childhood. I'm not this way anymore though and I've learned to accept it for what it is though.

When I have kids of my own I'm not going to put them what I had to go through