Elsewhere, I think a very big part of this has to do with the JW upbringing. We are discouraged from being social people. We are not involved in social activities growing up. We only associate with those who are like us, setting ourselves up to come across as judgmental, etc. Then others perceive us as distant and judgmental because we are taught to deem them as "bad association" and their reactions to us condition us to believe that we are socially awkward. And then we are. (My personal opinion on the matter, of course, for whatever it's worth.)
Anyway, I think everyone has given really great advice and ideas. I just wanted to share a couple of things that have worked wonders for me personally.
1) First of all, one of my best friends (who himself faded from the JW's several years ago and saw in me the potential of thinking outside of the WTBTS - it was a rocky road and hard on our friendship at times but he did it for me, not for him, and I am eternally grateful that he cared that much to help me see the truth) gave me a personal assignment once months ago to help improve my self confidence. He called it the ROCK STAR MENTALITY. We are taught our whole lives (if raised JW) that we are "good-for-nothing slaves" and "what we do is what we ought to have done" and "not to think more of ourselves than is necessary." Rock Star Mentality is not about being full of yourself. It's about recognizing how kickass of a person you truly are. And by everyone's posts on this thread alone it's obvious, Else, that YOU ARE KICKASS. :-D (And by that I mean super duper cool.)
So here's how ROCK STAR MENTALITY essentially works: (I was going to try and summarize it myself but I think it's worded much better by my friend so I found the email from him and posted it here; this is tried-and-true stuff. If you think it sounds silly, JUST TRY IT. I guarantee it!)
“Walk around one full waking day,
with your chin up,
and chest up,
so that you have proper posture,
and keep in your mind
“I AM A ROCKSTAR.”
Not in the traditional musical sense,
just in the self-esteem sense.
Not in an over-exaggerated tone,
like you are trying to convince yourself of it.
Like you are a super-star.
Like you are an undercover super-hero.
Like you are a true champion.
Keep a focus on this
anytime a thought pops up
of a self-conscious / self-aware nature.
When you find yourself,
being conscious of yourself,
good or bad,
just calmly and coolly remind yourself (even with a small smirk on your face) that:
“I AM A ROCKSTAR.”
Let me know how that FEELS for just one day,
you pick when.
(Remember the posture part, its critical.)
Again, I want to know how that FEELS for you,
just for one special day.”
Now, Elsewhere, I had so much fun doing this that I started doing it everyday. I worked at the same job before I started thinking this way and after I started thinking this way. Pretty soon I'm in the kitchen at work getting coffee and I'm getting asked out. I'm thinking to myself, "isn't this the same kitchen I visit everyday, the same people, the same me?" But no, it wasn't the same me. My self-confidence naturally projected itself to others and suddenly they noticed that I'm someone they want to know.
2) The second thing that works really well for me in striking up conversations with strangers is just to smile and make eye contact with someone. If they respond to it, say hi. Then let it go from there. If they look away, it's their loss. No harm done. Most likely they will be thinking to themselves, 'why'd I do that?' Seriously. I know I myself have thought that when someone tried to smile at me and I nervously looked away and then just walked away feeling dumb. So it's not you, it's them. Seriously. But back to if someone does respond to your friendly smile: you are usually both at the same place because of something you have in common so you can talk about that. Ask questions of course, saying something as simple as this works: "Wow, isn't it a beautiful day today? Hopefully you will get to enjoy it rather than be cooped up inside... [wait for response]". For me, it's much easier to just seek out friendly faces and say hi rather than think up some witty thing to say. Once the conversation gets rolling you will find that witty things will just pop into your brain. Because you've already established that they are interested, so you can feel comfortable in your setting. That's probably why it's so easy to post witty comments on JWD, because you feel comfortable in your setting.
Anyway, those are things that work for me. And I just wanted to share. Best of luck. I'm sure you are a WONDERFUL person.