How to talk with someone shy if you're shy (and other convesational skills)

I've noticed that one of my problems is that I find it vey hard to establish a good conversation with the opposite sex, it's either that I stick with a single topic or just plainly kill any possible way to continue with the conversation, and I usually just end up asking questions, which I guess ends up being really annoying. But when I try something else I just don't know what to say after hours. It doesn't help that the other person is usually an introvert like myself. Zetsuboushita guys, any advice?

I really have no idea. I am pretty shy myself in some sense. I am not afraid mto talk, I just dont like talking too much. Depends on the person I'm talking to tho. My Idea is that you either try to get drunk, which will reduce your shyness, or if you want to keep your liver you can practise ..I dunno talking to yourself when nobody isd at home besides you. Sorry that I dont have much good advice :S

I got you guy, One method is when the other person answers your question, figure something to say about their response that establishes a sense of commonality between the two of you; then ask your next question. This way the other person has grounds to make a small remark that isn't an answer to a question. I know that was a lot of words. Basically, say you ask the female what type of shoes she likes (just off the dome), she says sneakers (I don't know what shoes females wear) . . . Make a statement about how you feel about sneakers (don't worry about trying to sound cool, sensitive, smart etc etc. But try to make it something random and memorable) then ask another question completely unrelated (skyscrapers). Along with answering your question, the female will have a reply to your sneaker comment. Keep repeating this process and eventually you won't have to ask questions, you'll just be talking and she'll just be talking back. Hope this makes sense and helps you out

Honestly, I'd say practice. Make small talk at work, school, out somewhere, that sort of thing. It's hard to describe a method, in my opinion at least and especially in text form, for keeping a conversation flowing. You just gotta get a feel for conversation flows

Also questions are bad, but like build up on it. Ask a questions, comment on the comment, something like that. Hahaha it's hard to think up random conversations, but yeah. Build the momentum

Close your eyes and try to do something or say something silly, Laughter is a great key, once found that out it actually helped me overcome being shy, not my problem is figuring out when they actually like like me or am I just in the friend zone :T