This is a serious thread, despite the title.
How do I start being meaner to people? In a sense make 'playful' insults/jabs at people I don't know? All these pick-up books have it as practically the #1 cardinal rule, and even work it seems to be necessary. My boss makes jabs all the time, and I think I need to start making them to him (VERY informal workplace btw).
Thing is, I always picture myself in the shoes of that person, and I remember being a kid being bullied...and I hated all the teasing. Feels pretty mean, even if playful. I feel like I'm doing what I most dread onto others. Insulting people for no reason is like a personal phobia of mine.
How do I shake this off? Should I shake this off? I like being nice to people... I don't mean "oh ill lick the floors to please you!" way. That's ridiculous. I'm from the Big Apple, so fvuk that! More in this way: I see myself in other people's shoes. Unless its for a dire reason, I would never want to do something that I would hate to experience myself. I like being friendly. I hold doors for people (an art most selfish assholes forget nowadays). I say "Thank you" and "Please". I give directions to strangers, if I can (and feel shitty if I was wrong). Too many people nowadays are too ungrateful, self-assured, and...well...asshole s that I prefer not to join that realm of society.
...but I also want to make my boss comfortable around me so I won't get fired from my 1st out-of-college job....and be able to get a girlfriend rather than frat house hookups from drunk chicks who didnt have the sense to know that I'm an overly-emotional putz would be cool...