Trying to talk to strangers - Weird mood about it

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So I was out for a business meeting in a mall today and I figured out that I'm not using my social skills to their full potential. Walking in and out, there are a lot of people sitting around and or standing looking over WEM's Santa Maria (the malls main tourist attraction) that I could easily strike a conversation with. Thing is, I find myself overthinking my approach to conversation with any given stranger. I think things like "oh, they seem busy on the phone" or "oh, they're waiting for someone so I shouldn't bother them" or "hey, they probably don't want to be bothered, they're there to enjoy themselves watching skaters or something." All that, and of course, thinking "I don't want to be a creep" (A bs thought if ever there was one but one I still have). I want to dismiss this lack of wanting to converse to some sort of social anxiety ... thing is ... this action paralysis when it comes to talking to new people ... that's so common, calling it "anxiety" is overstating the issue.

In terms of how I view others, I'm mainly an observational but, unless approached, I will not go out of my way to interact with others. I will notice ticks, habits, mannerisms and tone of speech in terms of getting a read from someone (for the sake of it, of course) but I've never made any material growth in using these observations in way to initiate contact with someone and carry one a conversation. You see, I'm fine if someone starts talking to me, of course, but when I want to talk to someone I get a huge swirl of thoughts, doubts and, for some reason, painful reminders of when I have at some point earlier weirded people out (at least from my perception) with previous attempts at trying to talk to them.

My fellow aspies who are anxious about conversation and connecting with others, I'm reaching out to you. For those of you who are more extroverted and actually enjoy talking to people right out in the open, help me with my baby steps. Where should I start in terms of getting over this issue of starting convos with others?

I relate to pretty much everything you just said. Like, hit the nail on the head status. Thank you for putting this into words as you have saved me the trouble of forming them myself!

I don't think I can be much help and I'll be watching for others' feedback, BUT one thing I can say about this is from my own observation:
the longer I wait, mull it over, recite and edit my "script", reassess the situation, and flip back and forth between "now's a good time" and "they wouldn't want to talk right now", the harder it gets for me to actually just DO it, but also, the more likely it is that when I DO say it, it ends up awkward and unsuccessful.

I feel like one of the tricks is to just really allow yourself to be impulsive! Instead of thinking it and then saying it, externalize it on the first try. Easier said than done but.... sometimes it helps to imagine that the other person is someone I know. Lol.

i have several "ping" lines i use to start a talk. something short, polite and not very loaded. weather. price of bus ticket. its cold. its hot. oh, dont u know by a chance, who forgot that glove under the bench?
even if answer is closed, it wont be so embarassing as if starting with something deeper. but if answer is open (as in, long, and ending with a question or querry), then it went well. sorry, if i crample it. im not in a good shape this time.

I walk and hike a lot, and I do try to go when there would be fewer people in the park. But when I do come across some people on the road/path/trail, I feel like I have to say something. I feel weird not to. But in this instance it is usually a hello and a comment on the weather of the day or something about their dog if they have one. That is usually it as we are walking in opposite directions. When I am in a mall, I usually don't talk to other people.

I also notice that with most people it seems like I am the one that needs to instigate a conversation. Like you, I don't have too many issues if someone strikes up a conversation first. If that someone is a stranger, I wonder what their angle is. Why are they talking to me? Is it a ruse to rob me? Or just someone being friendly?

And like banana247 said, the longer she mulls something over, well... by the time I have figured it out, it is too late with the situation changing. It's like when I am with friends and we are talking about something, I always have a great line 5 minutes after the fact.

ya successful smalltalk is great xD
i just well, know over the years that its usually not that scary
employees at local shops all recognize me and often say hello first.
and if success doesnt happen, i dont let it get to me. that other person could have issues too, after all)

Years ago I used to do announcing. Talking into a microphone was a good way to learn about talking to others, although it was one-way. I also always could get a laugh in a meeting at work. When people laugh (not at you but as if they are amused), it feels like connecting.

When I was younger I was shy and unable to really initiate anything. It terrified me. I took some foreign language classes in college. When they were more advanced classes they were smaller, and a lot of conversation occurred. I think this helped get me started.

Now the disclaimer: All this means is that I can fake it pretty good. I still despair at having mostly little or no connection with others. On the other hand, I have a lot of superficial conversations that I don't think are bad, especially when compared too the terrified withdrawal that I had when I was ten years old.

Now Edmonton is way out there. People in Alberta are a little reserved, but up there maybe it's more of a problem. The main thing I think you should note is that you need to have a reason to talk to anyone. It can be a simple reason, but it has to be a reason nonetheless. Unlike some of the other suggestions here, I often find that a question is a pretty good opener. For example, if someone were driving a very unusual classic car, it would be an obvious thing if you knew something about that type of car to ask the owner some questions about it. This almost can't fail, because the person you ask is guaranteed to be very interested in the subject. Sometimes in social gatherings, I imagine I'm a reporter like Ed Bradley from 60 Minutes, interviewing someone about a subject. It's a delicate trick but you can get people into talking about themselves if you work at it. Of course the problem is that a lot of them won't think to ask you any questions so it's not all that two-sided.

Another suggestion I have is spend a week or so in a place like Boston in the United States. Strangers love to talk there. Even being a little shy about this, I had conversations with strangers there that went on for 30 minutes or more. And trust me, I'm probably perceived as weird like you say you can be. As for Canada, the people in New Brunswick seemed to me to be fairly chatty.