A long time ago I read an article about pronouns in Japanese written by the Yale Anime Society.
Fortunately, a quick Google search taught me that today there are many better resources about pronoun usage in the Japanese language (Wikipedia and Wa-pedia for starters).

But, when I read that Yale article, it really stuck with me. I thought it was the definitive guide to pronouns in Japanese and even made detailed flashcards for myself to remember who says what pronoun when. I'd taken the article completely out of its intended context (anime) and thought I'd meet people in real life using sessha or atai. Fortunately, observation of Japanese friends over time let me realize that what I'd been taught was horribly incomplete. I generally agree with the content of the Wikipedia and Wa-pedia articles linked above, but it's still, really, a long list of words from which only a handful are ever realistically used. For what it's worth, here are a few of my observations about Japanese pronouns.

私 (watashi) -
This is the starting place of Japanese pronouns. Brand new (native English speaker) students of Japanese pick this word up on their first day of class and subsequently pound it into the ground.
WATASHI wa Amerika-jin desu. WATASHI wa suki desu. WATASHI wa toire ni ikitai desu.
WATASHI. WATASHI. WATASHI. Even when the sentence doesn't have anything to do with you, or me, or even people at all, it somehow always begins with "watashi wa."
But, as a language learner myself, I can appreciate that. When you start out learning a new language, you're trying really hard to understand how words fit together, and a natural place to turn is your extant trove of information about your own language. "I" sentences are extremely common in English and consequently easy to build and use in early Japanese practice. With enough time and practice, beginners start to realize that Japanese people don't start sentences with watashi very often, and in fact they profusely leave out topics and subjects and all those things our English teacher told us are absolutely essential to a complete sentence.
So, to those of you mangling through your first few months of Japanese, spouting a "watashi" with the consistency of Old Faithful, I tip my hat. You're doing what it takes to get fluent, without fear or embarrassment. Keep it up.

僕 (boku) -
Boku is where I draw the line. This word is the ultimate pitfall for foreign guys in Japan. While I may fidget when hearing absolute newbies repeat "watashi wa" like a broken record (before remembering how brave they really are), seeing some big American guy with passable Japanese referring to himself as "boku" actually causes my stomach to churn.
Boku gets introduced by Japanese girlfriends to their boyfriends or Japanese professors to their students as a "cool" alternative to watashi. The thing they forgot to mention is: It's actually not cool. At all.
Just take a look at the other people using boku. Their single most common feature is a lack of pubic hair. That's the associated image. Guys who use boku after their early teens sound perpetually stuck in childhood; they failed to grow up and are thus woefully unprepared to be a productive, interactive member of society.
Your 40-year-old female coworker and the girls you practice "English conversation" with will clap their hands and tell you your Japanese is great when you start using boku. But, the word on their minds isn't "cool" or "dependable." It's "adorable." Like a penguin at the zoo. Everyone fawns over the penguin, but no one takes it seriously.
So, don't be a boku person. Please. Save your boss and your (male) friends the restrained shudder of embarrassment they feel every time you break that word out.

俺 (ore) -
So, what do manly men use? When talking among male friends, ore is pretty common. Just don't use it towards your boss or a stranger.
Ore gets shared usage among street punks and Japanese guys who think they are cooler than they really are, but if your dress, mannerisms, and the rest of your speech are up to snuff, referring to yourself as ore will bring you a quick-witted, wordly air.

私 (watashi) -
Yeah, that's right. It's watashi. Again. Not only is this the starting place of Japanese pronouns, it's the ending place, too. When you get out to the working world, writing self-introductions for job interviews and engaging in obligatory enkai parties with supervisors and bosses, watashi is really the only acceptable, professional-sounding pronoun. I think a lot of foreign learners migrate to boku (or ore) because they're afraid watashi makes their Japanese sound too elementary. But, as you progress in other aspects of the language and learn to express yourself clearly, I think reverting back to watashi, at least in your professional life, sends a subtle indication that you really know what those textbook lessons about "maintaining appropriate distance" in Japanese relations are all about.

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