I can't make the conversation interesting, I would like to ask the type of questions that lead to what's the craziest thing you've ever done type of stuff but It's complicated, here's an example of one of my conversations.

Me: Hey now, if your going to keep looking at my page like that im going to at least need a name

Her: Haha it's Katie

Me: Cool, I'm Nate. What part of cali did you grow up in?

Her: Northridge. You? And my brothers name is Nathan too haha

Me: I was born and raised here in the a.v, and that just means your brothers awesome haha. Are you the youngest?

Her: Haha! No I'm the oldest. Are you?

Me:No I'm the youngest. That means we're opposites , Just out of curiosity are you going to Northridge state university?

Then I never got a message back, am I putting too much thought into my messages? Any avice?

If this is internet messageboard kinda thing... then you cannot judge on one event. Next time its yours?

You could have taken her response anyway you liked. Examples..

'I once dated a Katie, she would bring me great gifts from her work travels...'

'Urgh... Not another Katie... please tell me how you are different... '

'Cool, I'm Jesus. I can walk on water...'

Man there's so many things you can say to make the conversation more interesting straight off the bat. I find by making it 'jokingly fun' right off the bat then there's more room to ask questions such as ' What three items would you take to the moon if there was a Zombie apocalypse and there was a mass evacuation?...'

Content doesn't matter just keep it fun.

Finesse.

_________________
"Life isn't about finding yourself. Life is about Creating yourself." So what are you waiting for?

if you are chatting to some random girl on internet
like guys above said
you dont ask these boring questions
imho better dont ask questions
make your statements and make the convo fun

Say what's on your mind. It will be complicated if you try and make it complicated. Just tell her what you want. If you want to ask a girl what is the craziest thing she has ever done, just ask her.

imo it doesn't matter what you say. The online world is so fearce she has already judged you on your pictures. Online in my eyes relies 90% on a good photo.

If she's just messaging you back generic stuff and not asking you any questions she isn't interested. If a girl is interested in you online you'll know it by how much better the conversation flows. It just happens naturally.