Me:
Hey there,
Do you like milk with ice?

Her:
Lol,.never tried it

Me:
Shame, strike one already :p but a chance for redemption. Do u like brownies with ice cream or without?

Her:
With

Me:
another strike, but you are cute, what's your name?

Her:
Jadie. And you

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I feel like I had a strong start with the lol but my inexperience is going to kill it, other than telling her my name how should i proceed?

thanks

What was the context? just a random girl you saw in the daytime? were you in a cafe or something?
You had a playful start, but i'm guessing you were just playing with this routine and not really enjoying the interaction. there are so many things you could have commented on after this. comment on her reactions, what she looks like or anything else you notice about her. But it might be good for u to elaborate on why the girl didn't meet your playful standards. That said, I'll tell you the secret of good conversations: Listening. You need to listen to the value she is giving you and comment on it. At least in the beginning of the interaction. The longer you talk the more randomly you can introduce new topics

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How to Get an Awesome Girlfriend
How to Train your Girlfriend