Okay...

[Cognizant]

I have no clue how to flirt with someone, or ask them out...

There's this girl I really think I like.
Jesus, I can't even have a NORMAL conversation with her without being awkwardly quiet...

Is there any hope for me? Any? Please help.

[Hank Hill]

Now, I'm not sure that this works for everybody but it's worth a shot bud,

Some girls respond differently when you're flirting with them. At work, there are plenty of girls that I "flirt" with, but I wouldn't really call it true flirting because I'm just doing it for fun, but I'd never think of a relationship with any of them.
What seems to work for most of them is just really small compliments, practical jokes (that are not mean), and being "fake mad" at them, if you know what I mean?

Those things return a really good response from most of them, but there's one or two that just get mad (or just not responsive) when I do that because they seem to be just irritated that I'm doing it. So, from that I think it changes from girl to girl how you should flirt with them.

Also, I have the same problem. Whenever I'm in a group of people, I'm outgoing and funny, and am really open to flirtation. However when I'm alone with somebody I like, at least in public, I can feel myself withdrawing and becoming quieter. I don't know how to fix that, because I haven't figured it out for myself yet, ha!

Maybe try one of those three things I said in the middle of that novel, and see how it works out for you?

Sorry I couldn't be even more help, but I tried. :D

~Tyler

[Cognizant]

I appreciate your help greatly. Thanks Tyler! :)

[ImCoolBeans]

As Tweak for a Day said - compliments, practical jokes, being "fake" mad are all ways to flirt. Some girls don't like the "fake mad" talk though, so I might not give that one a go unless she seems up for it. Some girls also like all of that cutesy stuff, but that could be overkill if you aren't actually together.

Try to hold conversation and not let it just drag along boringly. If you have totally aimless conversation then she probably won't be so interested because its well... boring :P. But if you are able to hold conversation with her then you've got a really strong foundation to build off of. Don't try too hard to maintain conversation and certainly don't try to be somebody you aren't - girls pick that up pretty easily and really are not into it. If you be yourself and treat her well then I think you're off to a good start :) Nobody does you better than you do, don't forget that.