hey there,
When I approach people I remind myself of how we are all human beings having an amazing experience. I've been entertaining the belief of subjective reality and its implications on social interaction is amazing. Through this perspective, how can I fear interaction with another part of myself? I become extremely curios and equally authentic in sharing my experiences.
Through my experience, higher level beliefs aid profoundly in connecting with others - you may wish to start here first.
Specifically (lower level approach), perhaps in the future you could introduce a topic yourself and begin the discussion with a short story instead of simply presenting the topic and hoping the recipient will elaborate.
From the PUA frame, this could be seen as immediately demonstrating higher value (DHV).
From the transcript of your interaction it seems there is emphasis on you extracting value ("Do you talk a lot to mutual friend?" "So, how is school?" "So, what kind of job are you going for this summer?") - I'd focus on giving value (the universe - including others - respond in kind).
I'd focus more on relating to the themes behind the subject matter when conversing especially if the subject matter doesn't resonate with you. e.g.
"law internship in summer" = future, goals
"Professor Wilkes won't release our grades" = adversity, trouble, challenge
"Can you believe that Suzy and Bob are dating now?" = love, romance, passion
I find its easier to share and relate on a more deeper level through the themes behind a discussion
