All my life I've always been the quiet one, never really talking to anyone who wasn't a close friend unless I had no other option.

Over the last few years I've gotten less awkward around people, and over the last few weeks I've made an even greater change for the better. I've started trying to see the world from a positive perspective. I used to hate A LOT about myself, but I'm getting over being to hard on myself, since I'm realizing that being comfortable around people and comfortable with myself is a skill that I think I have the potential to learn if I go step by step, since I see myself as a potentially likable person. Getting rid of the voices of self hatred was step 1, but I need help from you guys with step 2.

Step two was going to be going to the park today and starting a conversation with at least four random people. The thing is, for me, I think this was too hard. I passed by tons of people I probably could have talked to, but I just couldn't think of anything to say to anyone! Even just "hi" felt like too much of a challenge. I don't think this was anxiety. It was just thinking too hard. I need something a bit easier.

BTW, I'm not even thinking about hitting on girls yet. I believe I need to get comfortable around people in general first.

Any advice from someone who's been in my shoes would be greatly appreciated.

Ah yes, the newbie challenge. Maybe a good opener would be a simple compliment about what they are wearing or a response to something in the location?

Karoake...and no I'm not joking.

I used to be much the same way. I got over it a little bit, and then a local bar that a friend of mine worked at started having karoake night....I became a rockstar.

It's basically the concept of running before you crawl.

I can't sing, I know that. But I went, and I sung. And for a while, I could have gotten away with murder in that bar on a tuesday night.

The key to doing successful karoake is to not pick a slow song. While the whole bar may sing along to "Lips of an angel", it's not going to help your confidence level to stand still behind the mic singing the lyrics. My personal first song...Rockin' Robin. Why? because it's fun.

Have fun with it. All of my songs were either fast paced, or at least had a fast paced chorus. "Hell Yeah", by montgomery gentry got the whole bar screaming the chorus at the top of their lungs.

Get up. Sing. Dance like a fool. Once you've made a ass of yourself in front of complete strangers, saying "Nice weather, isn't?" is nothing.
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"He out bopped the buzzard and the oriole." (Bobby Day, Rockin Robin)

what you are talking about is therapy for social anxiety. Nothing wrong with going to a psychologist.

If you don't want to do that, then you do it the old fashioned way which is force yourself to talk to someone, anyone, every day that is a total stranger. Learn to make small talk, men, old ladies, everyone. Do this every day of your life and it never ends. Its not as bad as it sounds, store clerks at checkout counters count.

the outrageous challenge, or the "newbie challenge"....

this is also a therapy technique made up a long time ago by a pioneering psychologist.

I say if you can't talk to strangers, DO NOT do any of these "challenges". They will do nothing but cause you to freak out and you won't learn anything except that people are scary and mean. If you already have some real world practice with strangers then whatever happens in the "challenge" can be taken in proper context and you will laugh about it later.

As far as a challenge, if you are ready, here is one I got from a social anxiety website

"Today I went to a mall in the afternoon and took a walk around for about an hour. What was different about this time was that I wore two obviously different shoes and put a black mark on the side of my face. I was encouraged to do this as part of my exposure as directed by my CBT therapist. No one said anything to me. No one even gave me a second look as far as I could tell. This exercise is supposed to show me that most people are engaged in their own life and couldn't give a damn about me."

1. It just feels strange though to complement a stranger out of the blue. I don't see anyone else doing it so I feel like they'd pick up on the fact that I'm a bit uncomfortable. If there was something I could comment on that would make it easier, but I couldn't think of anything today. This is probably what I'd be most comfortable with though.

2. I'm not 21 yet, so going to a karaoke bar isn't an option. But it is a good suggestion, maybe I'll try it when I turn 21 after a drink or two.

3. I do see a psychologist. We sort of just talk though, but I guess it's helped, or at least prevented me from getting worse. I also used to see a hypnotist but I strangely couldn't get into a deep hypnotic state, so I stopped.

4. I have no problem going outside and walking around. I used to, but I'm over that. I just need help feeling comfortable around strangers and setting realistic goals.

Ok, maybe I didn't say it clearly, but when you talk to total strangers, the goal is SMALL TALK , or CHIT CHAT. Its very shallow, not personal unless they make it personal, very rarely a compliment unless it is really sincere and you just want to tell them. It is not sucking up or being a bad ass, it is in the middle. You are assuming that both of you are just human beings who are going to interact for a few seconds or minutes. "boy the weather has been cold" that kind of thing. Or you go up to checkout at the drug store and say "wow have you been busy all day ?" Its just stuff like that.

"If there was something I could comment on that would make it easier, but I couldn't think of anything today"

don't comment on something really specific , personal , political, etc. unless you really mean it. the other person will read you and see if you are bullshitting or sucking up or playing a script or something. If you really do mean it, and its a woman, then say it. Being afraid to say a compliment you really mean is an obstacle.

Recently I complimented a woman I think was about 55-60 on her short hair. I told her I usually don't like short hair, but it looked really good on her. I honestly meant it, it looked good. Her face lit up and she held up the line for about a minute telling me how she had chemo therapy a few years ago and her never grew back right and she was so happy that someone liked it. That was like 3 weeks ago and I still remember it and it was just chit chat at the checkout. Its good therapy for you and the other person too. People need positive interaction.

Don't look at it like you are bugging them, because if you do it right they will look forward to it. The people at the convenience store down the street say hello to me by name when I walk in because of it.

Oh no, don't worry, if I feel like I'm saying something worth saying I can be pretty confident. If something pops into my mind I'll go for it, but thinking of things to say isn't always that easy. It's just a matter of getting faster I think, because sometimes after I say something I don't know where to go from there. But whatever, that'll be step three.

If anyone else has been in my shoes, let me know the first step you took to go from "oh shit what should I say to people?" to having natural conversation. Or it would be cool if I could at least get reassurance that there have been people worse off than me who were able to get over their issues, because I still sometimes feel that I'll always be stuck like this.