I've edited a few lines.
Mike: That girl in my class is gorgeous, I want to ask her out again.
Ron: That's very nice. I'll keep my fingers crossed for you.
Mike: Yea, thanks pal. We hang out very often. Last night, everything went perfect. We had a nice dinner and chat. She is not seeing anyone now, and I'm going to take a chance.
Ron: Cool, just to push the envelope then.
Is that alright? Hm, the decontextualized idiom is easily to grasp, but it's better to provide a suitable context to make sure understanding.
Not really better IMO :(
Let's see what the teachers say.
I believe you should say "we hang out together/with each other".
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