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@animeirl @Kirino @bot @Moon @zaitcev Okay, I’m going to spell this out in autistic terms, because it’s something I had to figure out myself. Some people are born knowing, others aren’t so lucky.

A casual conversation with anyone involves give and take, and the talking should be roughly evenly split between the two (though some people like to talk more, and some like to listen more, so it’s not a solid rule).

You can say a few things you think the other person will be interested in, see if they respond, and if not you can either keep talking or ask them a question to let them talk for a little bit.

The first part of a cold conversation with a stranger is usually going to relate to the setting or some superficial detail: “Hey, sorry, random question, do you know how late this place is open?”

An interested person will respond with something friendly to keep things going: “Yeah, I think it closes at 9. Planning to be here a while?” Someone who is not interested will just say, “Oh, sorry, I’m not sure.” and look back at their phone or whatever (this is how most people will be, so don’t feel bad if it happens).

And at that point, if the person is interested, you can start talking about whatever work you’re planning to do (or procrastinating on), comment on how you haven’t been there before or often, say it’s a nice place, whatever.

Your goal is to eventually get into more personal topics: “What do you do? I’m a __ working for __.” or “I’ve lived here for a while but haven’t really explored much, I realized there’s probably a lot of fun stuff around that I’ve been missing” or whatever. An interested person will start talking more, and at that point the most awkward part is over, though the whole conversation is still going to be sort of awkward because you don’t know each other.

Depending on how well it goes and how interested each person is, this could go on a while, but eventually it will start to slow down as both people come down from the little bit of adrenaline that comes from talking to a stranger. At that point you need two things: 1) a next step (“Want to get lunch sometime and show me around/I’ll show you around?”) and 2) contact info. For the next step, try to get a firm date if you can, but don’t turn it into calendar shuffling. If something like “next Saturday” works, great, otherwise coordinate it later. Keep the flow going.

For contact info, try to go for a phone number if possible, but some people may be uncomfortable with that. Normies may want to just be Facebook friends (adjust for whatever generation you are), which isn’t ideal, because then you’re just a +1 to their count and it removes a lot of mystery that you may want to keep at first. You want something more personal; even email is better, if a bit awkward (an interested person won’t mind). You just need some communication method to start with, and you’ll figure out what works best for you both over time: phone, text, chat app, etc. The important thing is to not make a big deal out of it; just get the contact, verify it works and that you typed it correctly or got the right person (important), smile, say see you later, and then leave.

Boom, initial contact made. It may sound so stupid and obvious, but this basic process is becoming more and more of a lost art as people get consumed by their phones and (anti)social media.