Start with small talk! It's so valuable in establishing a baseline of "we're two humans in the same condition at heart, and the first thing I'm offering is a universally shared experience, and not talking crazy to you or starting a fight (physical or political or otherwise)"
A lot of people think it's just useless filler but it actually is so important and a valuable tool when meeting people!
Talk about the weather! I'm serious! And drop any kind of internal pretension about being too good for such an inane topic (if that applies to you). Embrace it as if you're meeting someone from a distant tribe, and you are both wary of each other, and you want to start things off on a good foot. Talking about things you know you both deal with and think about is literally perfect!
I am a pretty asocial dude. But I think I can make a decent first impression by being a "social chameleon".
- recognize the environment you are in
- what are the common ideas that are popular within that space
- wait for a cue and say something interesting that opens up to a response
- listen and contribute to the conversation
- start by almost telling a story or making a comment.
- having a friend with you will 10x your confidence in being more open to these conversation
- make sure you are not tired and you really are committed to have a discussion
Recognize the fact you can't easily have a good conversation with a random stranger. You need to have something in common with them. The less things you have in common with them the more reluctant you will feel to invest in having a casual conversation with them.
I'm also fairly asocial. I can be 'on' for maybe an hour before social fatigue sets in. The bigger the crowd, the smaller the half-life of my social energy.
Much to my surprise, I volunteered as a door-to-door political canvasser some years back. It's not strictly out-and-about strangers as suggested here, but these people were unknown to me and I was unknown to them. It just happened to be on their porch.
I was initially petrified, but I figured out some extremely effective tricks to establish a rapport _before_ launching into my political script.
As I'm walking up to the house, I'm looking for decorations, plants, the porchlight. Especially the porchlight.
Ring the bell, knock on the door.
"Hey, good evening! Yeah before I get into that (gesture at campaign button pinned to my chest), I noticed you have a compact fluorescent bulb out here. And right away I'm pretty sure we see eye to eye on some environmental issues."
Smirk or smile. Instant connection. Literally nobody I used that opener on, ever turned me away. Which is a heck of a statistic given the overall reception that political canvassers got that year.
Things I'm not commenting on: The car in the driveway (not sure it's theirs), the trash in the yard (don't bring up a negative), the peeling paint (not their fault, they're probably busy, etc).
So if you're looking for a way to make a connection with a stranger, look for something they did _on purpose_. Not their physique, unless they're obviously a bodybuilder or something, that's usually unintentional and many people are self-conscious about it. But they definitely picked out that funny slogan T-shirt, or the buttons pinned to their bag, or the scarf in the colors of the local sports team's rival. All those things are statements they're making _on purpose_ to the world they're walking through, and you're in the clear to comment on them.
To add to the others comments about small talk. A big blocker to being able to small talk is self-centeredness / self-consciousness. A lot of people think that if they say something to someone they will be evaluated and that's almost never the case.
Unless you look homeless or like you are selling something, and unless the other person is mentally ill, they will welcome you speaking to them.
And then in terms of content, jokes, questions, and observations work well.
For example, if someone's with a small kid, I'll ask how old the kid is. If someone's driving a family SUV (something I know about from having shopped for one last year) I'll ask how they like it. Or just comment - I like your cars, actually considered it last year.
Make a joke, even a lame one. Long line at the coffee shop? "Wow I need a coffee just to get a coffee here!" Or even dumb stuff like "that's a huge menu, I don't see coffee on it"
Etc. The main thing is - if you are coming from a place of being human, it will come across as such. Content matters less.
I think context is key: who, what, when, where, why.
If I'm picking up my daughter from school, striking up a conversation with someone (i.e. another parent) would be totally different than making chit chat with someone at the bar/club. Often, the thing that previously held me back from talking with someone was fear of rejection, something I really struggled with in my early 20s and found that as I've gotten older (mid 30s now), I'm much more comfortable under my own skin and find it easier to approach strangers. I don't think the fear will ever disappear but, does get easier (in my case) with age.
A simple comment on the situation is a great ice breaker.
After that, the simplest trick is to ask questions that get them talking about themselves. Most people are more than happy to talk about something they're familiar with, so asking something that only they can answer ("So who do you know here?", "What do you do for a living?", "What are some of your hobbies?") will get the conversation flowing.
Anything that you both see happening. For example commenting on a cute dog passing by is a great conversation starter because everyone likes cute animals but everyone has a different opinion on what makes them cute.
Some people will go for your conversational hook and jump in. Others will ignore you. That's just life and normal, don't worry about it.
If someone joins your conversation, be sure to give them plenty of space and time to talk themselves. Most people who feel shy make the mistake of filing every conversational gap and every silent minute. But that other person maybe just needs a moment to remember a funny story to tell you.
Something situational. "This is a pretty good party! X always seems to do a good job getting interesting folks together."
Start small, work up. Don't start with a long story. Maybe skip the questions, which obligates the other to come up with something, making them uncomfortable. Make a statement about something neutral, or about yourself. See if it gets a response. No? Move on.
Specifically with cashiers at checkout, I find the question “has it been busy today?” almost always generates an enthusiastic response (“yeah, super busy!” or “no, not really!”)
