Rex Man said:
Man up fool! Have fun in the convo and others are sure to follow. It's better to be slightly too quirky than too serious. Once you open up the flow of communication and establish a comfort level; the other person(s) can jump right on the chat bandwagon. Do this: today instead of worrying about furthing conversation, just worry about your own pleasure and talk about things that genuinely interest you about them. Try it!
This is good advice. Conversation should always be enjoyed. It should never feel like a chore. It's fun.
This is a trick that I use with people that I've just met. When initiating the conversation, I talk about something I know.
Usually I ask questions that I would want to answer myself. For example. If I'm on a date with a girl that I've just met.
Me: So what do you usually do for fun?
Her: Oh, I don't know. I guess I just blah blah blah... What about you?
Me: That's cool. I'm into so and so, but sometimes I also blah blah blah. Have you ever done blah blah blah or so and so?
Her: No, but I've always wanted to try so and so
Me: Really? I usually go out to blah blah blah when I'm doing so and so. It's really cool and when I'm out there I feel so relaxed and calm. You have any places where you just feel like you can chill with no worries?
Her: Yeah, there is this one place where blah blah blah blah blah.
This is just an example. Basically the flow of conversation is to ask a question that you wanna talk about. Add your two cents to the conversation about that subject, then twist another follow up question with something she said while answering the first question or with something you said in answering your own question.