@Mattang - About your approach anxiety, that has always been a real killer for me and I have started to work on it. It started with baby steps as you have done, making small talk with random people. A key I have found was to make observational statements rather than questions because a simple question will usually only get you a simple answer; meanwhile, a simple statement can unfold into one of the greatest stories ever told (jk). Once you got the hang of that, you move on to the ladies.

Oh, and you definitely want to try an extra-curricular activity, group, etc. Even if you don't make the group, it's always a good way to meet new people, because they will often have get-togethers/socials. Say you always wanted to talk to this type of chick, join the African American studies club, Asian studies, Latina, etc. Maybe you're skilled/talented, join one an art club, music club, etc. and let your talents do all the Pick Up for you.

Anyway, yeah, pick up still works when you're out of college or at any age, but capitalize on college tail for now. You can get to the scalawags and the barflies soon enough, right now you'll just have to bear with all that college ass.

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"You ain't accustomed of going through customs. You ain't been nowhere, huh?"

Your problem is first and foremost your comfort zone. You've started down the right path, as International mentioned before me, by starting out small. What I've found is that as your comfort zone widens, your social skills will develop. By pushing your comfort zone little by little, you'll get there eventually.

Talk to strangers at the bar first, until you're comfortable doing so. Then escalate to the next level, by talking to strangers at the street. Once you've done that, you can start chatting up the girls you feel most comfortable with (as long as you still find it uncomfortable) and so on.

You should really complete this.

An awesome quote to end with: First you do the things you're scared of, then you get the courage.

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Alea iacta est - The die has been cast

Problem with observational comments is that people usually aren't wearing stuff all the interesting and usually after a comment like "hey cool watch" i'm left with a thank you and that's it. Usually I would say hey what drink is that?(Which i guess isn't a comment actually) or maybe do you come here often? Is there a lot of people during the weekends? Unfortunately these questions often don't lead the conversation anywhere. What would be cool is if I could get sort of a conversation starter or something to trigger an initial conversation with multiple conversation threads.
Yeah i've seen that before and since then i've been trying to make eye contact, smile and say hi to random people throughout my day. The mall would be about a half an hour drive for me so I wouldn't actually drive out just to say hi to random people seemed kind of pointless. Honestly though I think i'm past that i've done a harder newbie mission before. I asked 5 random people what time it was everyday. After about a week it got a little mundane and boring so i just stopped since I felt it wasn't very hard for me anymore.

I am also apart of a few clubs, like MMA, chess club, math team; not exactly girl-magnet clubs though hahaha.

You can observe other things.
Like walk up to a guy and say "Damn, the girls out tonight sure are hot"
Or to a girl "Is it just me, or do we have an awesome DJ tonight? Makes me want to dance"

You do not need to comment on something on their body. You could also comment on something else about them. Like:
"Hey, red dress, you look like you're lost in thought... You're thinking about ice cream, aren't you?"

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RSDTyler

If you referred to asking people the time as the harder newbie mission, I disagree. The whole point is to say 'Hi' to people without having an actual reason to do it. Once you have a reason, like 'what time is it' or 'where is the nearest Cafè', the whole point of the mission disappears.

However the same still apply. You have to push your comfort zone. Do things you're not comfortable doing, and when you're comfortable doing it, push it further.

MMA is cool. Both math club and chess club might not be the biggest turn-ons, but as long as you take pride in what you do, it doesn't really matter.

A small quote to have in mind; 'Life begins, where your comfort zone ends.'

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Alea iacta est - The die has been cast