I want to improve my social skills. I thought by way of stepping out of my comfort zone. So here’s what I thought:
Try and make conversation to a random person, location or occasion be damned, at least once per week. With saying more than two sentences be deemed sufficient. If the other person does not initially respond amicably (to the first sentence), I leave them alone.


It is a great plan. I recommend you do it in appropriate venues.
Bad venues:
Good venues:
What about a bench in a park?
If they sit down next to you, yes. If you sit down next to them, no.
It’s ok to sit down, say hi, and see if they respond. Maybe they’re trying the same process.
Yes, that would be a case of the other person following my rule.
I would think that is fine, provided it during a high traffic volume time period and with people who are already sitting on the bench.
Depends on how close to the playground you are.
If they ask which one is yours do not reply by saying you haven’t decided yet …
Seems fine
I dunno, is this a good venue? People are there to shop, not to socialise. Most people will likely want to get on with their business and get back home.
I chat with people in checkout lines… not protracted conversations.
Interesting, chat about what? I’m in Denmark and it’s rare that anyone says anything to someone they don’t know in a shop, unless it’s the customary “hi” to the cashier. Where are you where this is more normal?
It’s normal here (Florida US) “wow that’s a big watermelon”. “Looks like you are having a party!” “Hey, I haven’t tried that, it’s good?”. Or just weather or OMG your baby is so cute, or whatever. General small talk.
I remember once a lady saw me buying a diet coke and asked “does that work?”
I think the US is sort of a middle ground on random conversations. Not super friendly but not aloof.
In my case it is usually about kids that are with me or with them.
Public bathrooms are fine. You just have to make sure you get the urinal next to the other person.
Alternatively, if you’re in a stall and hear someone struggling, with flatulence for example, you should call out to them and tell them that you hear them and empathize.