How do you overcome the fear?

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Easiest way to me is to strike a common chord or talk about something both parties can see. if you have trouble with eye-to-eye contact, I feel that talking while you you're doing something - a bike ride for example can smooth out some kinks. But then again, zipping away on a bike going 10+ mph does take finesse.

Dilbert, people in mall wouldn't want to open conversations with strangers unless they personally know you.

Cashiers , baristas and waitresses aren't supposed to open a no-service related conversations with clients , you are not even supposed to waste their time with weather and other silly chit-chat , they have work to do , damn it. And some of them might be paranoid enough (due to their nature of their jobs which has a significant exposure to harassments) to call the guards.

And the thing you're suggesting is socially unusual and weird. When I am in mall I don't see guys talking to cashiers about weather and dress , all they do is paying them for the stuff they purchased. And when I am in a restaurant, I don't see guys conversing with waitresses or baristas.....

Surely your advice isn't common sense and isn't a common way to practice social skills.

Seriously...what are you inventing?

You're right Boo. But this thread is about getting rid of fear, and approaching people over and over again, often being rejected will wear it down to nothing.

Customer service people are paid to be friendly, so talking to them will reinforce confidence.
Random people in stores are generally in a hurry and don't want to talk, so talking to them lets you get used to rejection.

It's a two pronged attack against fear

Have you ever heard of "Archetypes" or a mental representation of something in your head? The reason I'm asking is because 5 years ago when I walked into the gym and started working out, I didn't imagine it was me. I felt like I was someone else, one of the healthy guys, someone who had a gf.

I'd like to tell you that you can switch to the "quagmire" archetype and have a party, but that kind of confidence has to come from somewhere. Have you considered putting yourself in a situation where you would have to interact with others? For instance, a volunteer group? That might take away some of the anxiety, you'll have an actual reason to talk to other people. You could also think of an archetype you like, by no means do you have to act like this archetype, just keep it in mind when acting.

Other ideas include remaining objective, and lots of physical exercise, not only do you feel less anxious after working out, if you have any of the jitters left, you can chalk it up to working out, there aren't many people out there who will hold that against you (unlike the AS)

Dammit man! Stop making excuses and just do it. Or learn to live alone. Those are your two options.

This isn't my advice actually. I've heard this advice used many times in various forms. If you are socially awkward you must practice. To improve your socializing skills and to get rid of the fear. How else are you going to learn?

Or like I said, accept yourself as you are and be alone, if you think you can.

Not whole conversations but one or two sentence exchanges between strangers are quite common. I do it all the time. The key is that these mini-not-quite-conversations are generally only 3 to 4 sentences total. You say something, they say something, you say something that closes the conversation. End. I routinely talk with cashiers, waitresses, clerks of all sorts, bus drivers etc. for 3-4 sentence exchanges and I'm not the only one doing it. Much of what I say is just exactly as Dilbert has outlined it.
Weather example
Me: It's pouring out there. Hopefully it stops before you get off work.
Cashier: I hope so too. I forgot my umbrella.
Me: That sucks.
End
Oops that was 5 sentences. But anyways it is meant to be light and short and not to impose on them. By imposing I mean that if they are in your age bracket and nice looking, it should be sufficiently light and short that they are not on their guard that this is a prelude to asking for their number. Because it shouldn't be. This is just to get the rusty gears of light socializing going. An end in itself. No ulterior motive.

If this seems impossibly daunting, try it with middle aged or elderly women. We are a chatty bunch and will make it easier for you than a man or a beautiful young woman.

I would never try to chat up a waitress or store clerk. As someone paid to assist me, they're a captive audience, while I try to make it clear for my own sake that they can stop talking to me and leave if they wish to.

Hahahahaa

are you talking to me or to TOS?

because I have no fear! I have no social phobia.

I talk with customers every day , with strangers and with partners (bank's CSRs).

I rarely chit-chat with customers , I tell what they want to know and answer their questions.

Sometimes, I chit-chat with the CSRs , most of them are females btw, but not to the point of wasting their time or distracting them. Most of the times, I usually go directly to the point but most of those conversations are done by phone.

Not to mention the chit-chat with my coworkers.

I don't need more exposure , I am already practicing. I don't think talking with random people would add anything.