Wonderful story!
(by the way - it reminds me "Gatsby". The same feelings)

"I should be calculative, enigmatic, cool".
Oh, yes! One time I was in the same situation, like this guy. But there was another finale:

• Well, I am not Gatsby. I am just a rude guy from the getto. But this fact saved my mind.
• Saved your mind... and your life. If you're comparing yourself to Gatsby)