"Andrea, you should send an email to that person you admire/introduce yourself to that intimidating individual/ask that cute boy to hang out/strike up a conversation with a stranger/saddle up to the bar next to that ridiculously attractive hipster. What's the harm? You know you want to and the curiosity of not doing it will (someday) kill you."
"No, you shouldn't, and here's why: Your chances always end badly. You have more strikes than successes, my friend, and as one half of your psyche, I'd rather not deal with aftermath of yet another heartbreak."
"But not all of those chances went terribly. Some of them ended quite well! And maybe this could be one of those times. You never know!"
"Oh, you optimist, I do know. Think of all the past humiliation, was it really worth it? And even more importantly, if these people wanted interaction, wouldn't they have approached you?"
"Maybe they're shy! Maybe they're scared! Maybe that's why I have to be the brave one!"
"Maybe they don't care! Maybe they want to be left alone! Maybe they think you're weird and gross!"
"It's better to know for sure than to never know at all. Plus, all those horrible moments make for great stories."
"Ugh, you and your stories. "
"Fortune favors the bold!"
"Just leave well alone!"
(Around this point, I typically flip a mental coin to silence them both.)