I actually don't have a problem with talking with girls. No more of a problem with girls then guys, but I don't know what to talk about. I usually follow the lead into conversations, and I usually don't engage in conversation enless they are a close friend, and even then I sometimes don't. Its not a fact of opening up, its just that I don't have anything to talk about. I am content with just thinking to myself. But anyway, I like this girl at my work and she said that she's shy too, so I have no idea what to say when we are just standing around doing nothing. Im great with my other co-workers, they always find something fun to talk about.

I hear you. Might have to consider the two of you are not conversationally compatible if the talk doesn't flow naturally and you're not inclined to come prepared with a list of conversation starters.

Something to break the ice, and it works because if they don't know about the Yankees it's still funny.

"How about them Yankees?"

Or anything stupid/funny, it works with girls you know. But don't do it with a stranger, they'll think you're a psycho!!

Conversation isn't a "trick". It's a natural outcropping of having things going on in your life and simply talking about them. If you don't have ANYTHING going on, then you aren't going to be interesting... unless you're naturally funny.

Conversation is about making a comment about something factual, historical, experienced, felt, purchased/returned, offended, complimented, work-related, family-related, dreamt/hoped-for, etc.

Surely SOMETHING on that list applies to you? Make a comment, then ask a question similar in topic that isn't a 'yes/no' question. Her answer to your question should create multiple thoughts of your own to follow up on.