How do you talk to someone for the first time?

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I've actually come a long way with starting up conversations with random strangers. In California I never learned this because it was best NOT to talk to strangers, but here in the South everyone is so open and friendly that it just comes natural after awhile. I usually just start out with "Doin' alright today?" and depending on the person they either open up and start talking about their day or they end it quickly. A lot of times I'll ask them if they have any plans for the weekend (in a non I-want-to-date-you sort of way).

Something vague. Like the weather or asking them what time it is and that can start a whole conversation.

When is it dangerous or dumb to talk to a stranger? <---maybe this should be another post.

Person is walking on the sidewalk, right in front of you, and it is dark. You have to be 100% sure that whatever you will say to that person will not make him / her paranoid.
You are walking, and you turn around to talk to the person. <----not a good idea.
Person is way too young. Someone can think your intentions are very malevolent.
Person is way too old. This one happened to me. The guy could barely hear me. He was kind of deaf.

I find it very easy to talk to random people, random hot girls, somewhat harder, but still easy for the initial conversation. I used be shyer, then I spent a few months in jail, then my thought process for people on the outside for approaching them became "will this person punch me if I say X to them?" As far as talking to random people, it's more "Just do it" that comes to mind. I made lots of acquaintances and a few friends from talking to random people, plus lots of useful info.

Random people is a good test, as you almost never have to worry about seeing or choosing to talk to them again, so you can be a complete fool and not care I found out. My problem is, especially with girls, they don't read car magazines, or do much of what I do at all, I can't go talk about small block chevys with them or whatever, you know? The other problem after, even if a girl falls head over heels for me, uh, then what do I do?

To me, random people are the easiest, the hardest thing is small groups, as there's a group dynamic of sorts that has to be worked with, to fit in, but be an individual at the same time. Big groups, random people, hell, I'll prolly never see them again anyway, so I now lack fear in that regard.

So yeah, to put it shortly, just do it, and for me, I just think when was the last time some random dude at a fair or on the street wronged me significantly? Like never. It's mostly "friends" that hurt you the most. Maybe that's a little pessimistic of an outlook, but that's how I talk to random people.

It can almost be a challenge, too, a way to test social skills without getting hurt, seriously, it's very unlikely someone's gonna fight you, and if they say something not nice to you, screw it, you'll probably never be forced to talk with them again. I guess also be friendly and don't be a dick, too.

If only "connecting" with people for real was this easy...

I have a hard time to trust strangers. If they initiate a conversation or there is no chance I see them again, there is less of a problem.

When there is someone unknown in a city, and there are many people around, it is very often me that they pick, and asks where some street or building is.

When I want to talk to someone I try to have a topic in mind beforehand.
If this is an acquaintance from university/neighbourhood/insert other unlikely place here I try to find something we have in common and try to build things from there. At uni I try to avoid the typical how are the classes going?but if I cant find anything else suitable I use that.

For random strangers I try to look for a common interest(theres usually one if you think hard enough)and if there isnt I use my small talk "skills". This is a last resort because I fail at them.
Just so you have an idea a couple of years ago I was in a foreign exchange student program and an acquaintance(was at my classes never talked)started talking to me. She asked where was I from and I answered. Five minutes later I decided to continue the conversation by taking a guess where she was from(and failing at it).
She found it funny and we eventually developed a proper friendship but most people usually left at some point between the 5 minutes break.

My small talk skills are somewhat better(9 months abroad/switching schools twice pretty much forced that) but I still struggle making the first approach.
A more recent example:
The last time a girl joined my study group she ended up asking if I had anything against her because I hadnt talked to her in 2 days, the rest of the group mentioned her that it was just my normal behaviour and I started talking to her after she said that.

I'm really not very good at approaching people, small talk, etc., however I've found the following conversation starters to be somewhat effective:

1. "Would you like to come see my basement?", and
2. "Does this look infected to you?"

Used to be super shy about approaching strangers...mostly because my AS mind would draw a rational set of conclusions that fed upon themselves until paralysis set in: what if she talks to me back? What will I say? What if we hit it off, and start dating, and then get serious, and then marriage, and then what if we fight, and get divorced.... my mind would always create these scenarios, and it would paralyze me.

More recently though I've been practicing and practicing at being in the moment, and just starting conversations for the sake of conversation. A lot of practice.

But there has to be something to talk about...can't just walk up to someone without any context. That comes off as creepy I've learned. For example, I've just flew back to LA from Indianapolis and was seated next to this very lovely woman. Now typically I wouldn't even bother striking up a conversation with her in this sort of airplane situation, because she probably gets bothered all the time -- and I don't want to be THAT dude on the plane that won't shut the f**k up. But as I pull out my Harry Potter book to read, I glance over and notice that she's reading Harry Potter too. So I just sort of blurted out how amazing it was that we were both reading Harry Potter. Turns out we were also both reading the same book (Goblet of Fire), and that she was only 20 pages ahead of me.

Of course that was a natural conversation opener, and it just sort of took off from there. We talked for about an hour -- with her asking as many questions of me as I did of her. After the snack cart went through, we sort of went back to our own little worlds...but goes to show you really NEVER know.

It doesn't however, make up for my complete inability to make conversation at the GenCon event I went too, lol. It was the perfect venue for me to talk with geeky girls, but somehow I was too intimidated by them, lol.