As a middle aged man (at least on the outside!) which should I use?
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This probably isn’t explained well by textbooks and whatnot, but a single person can use multiple pronouns, adjusting them to the situation.
You would want to use わたし or わたくし in formal situations. ぼく could be used when you are talking to people who are senior to you. おれ when you are talking in casual situations with people younger than you.
It’s not that you just choose one, though something like わたし or ぼく is fairly versatile.
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Thanks for that. I never gave it much thought.
Use 俺様. It’s what all the cool kids say.
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Generally, you’ll want to use おいら or あたし in 99% of situations.
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吾輩, of course.
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儂 master race
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I prefer to use あっし for that special snowflake factor.
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But if you really want to impress everyone you should use [ 我々 ]
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I sense a certain level of piss take in some of the responses。
Whatever happened to respect for the elderly…
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Oh, you didn’t say you were elderly. Definitely わし, then. 
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In casual contexts, choosing between 僕 and 俺 has been a tricky decision for me.
But currently, around my close friends I still usually go with 僕.
I don’t know, 俺 seems a bit “rough” for me, and personally I don’t really identify with it.
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In all seriousness for the original OP:
私 - formal and can be used by both men and women.
僕 - Used only by men and less formal. I use it with my boss and co-workers, but not my boss’s boss. I will also use 僕 when chatting up the ladies at my local bar.
俺 - Super informal and used only by men. You should only use it with your homies.
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Ok thanks. I was just a bit worried that 私 would sound a bit wet.
Two more days until we fly for Japan…
What are you doing there? Just travel? Using 私は or other variations all the time will make you sound like a complete noob, but whatever… Like, if you’re asking for directions you don’t need to use it. Just drop it 90% of the time.
Yeah, I’m trying to remember if I used any pronouns at all on my last two trips…
In everyday speak or written Japanese, I find you only need to use 僕は etc to make it clear that you’re talking about yourself. Otherwise, it’s obvious, so 99% of the time it’s unnecessary to use. That’s inexperience for you. Besides, people will use all sorts of pronouns to refer to themselves that the rules are not clear at all.
In general though, あなたは I would say is quite rude, and rarely used. You should use the person’s name instead.
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I use わたし almost exclusively. I’m a noob I guess.
It would just feel weird to use anything else to me.
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When I was in Japan I tried hard to use あたし but honestly I ended up feeling like a complete weeabo, you know… “ooo look at me, obvious foreigner using non-standard pronouns!” I switched back to 私 very soon and just stuck with that.
Not saying people using anything else are weeabos, but I certainly felt like one 