We live super safe lives nowadays. Which is none of my business, really, but it should be of yours. A safe, sheltered life hardly makes you a better writer.
Get out there and do stuff you would never do. Observe other people. Stare and eavesdrop. Be naughty.
Go to a rich neighborhood in the morning as people go to work and a shady neighborhood after dark.
Be kind to someone who’s rude to you, or rude to someone kind (you don’t have to be very rude, just act like an entitled prick and set yourself up for failure, so you’re easy to tell off).
Even if you never went clubbing in your life, go at least once to see how it’s like. Party with complete strangers, and drink till you pass out (if your dignity can stand it).
Help strangers in need.
Talk with people. Show interest and nod a lot. People love talking about themselves.
Go and have a heartfelt conversation with one of your friends. Ask them about their life and problems, and then really listen. Everyone has a pressing issue they’re working through. You’ll be amazed by how close this can bring you.
If you’ve never been in a fight before, get into one. A black eye lasts only a week or two.
Stand up to a bully. Better yet, do so in someone’s defense.
If flirting isn’t your thing, flirt. With random strangers, if you must. Whatever happens should be quite interesting.
In general, try to do stuff you haven’t done before. Fake it if you must, it doesn’t matter. You will learn loads about other people, and maybe even more about yourself.
Here’s an anecdote; it’s absolutely true. Ask any of my friends.
I once made a rough-looking character pick up the dog-end of a cigarette he flicked onto the sidewalk.
“Hey you, pick up that dog-end,” I called after him.
He turned around and approached me. “Or what?”
“Or I’ll knock your fucking teeth out.”
I would do no such thing, of course, I don’t think I ever managed to knock out a single tooth from anyone. But I looked him squarely in the eye and spoke his language, just to see what would happen.
He picked up the dog-end and walked away without a word.