The choice of pronouns mostly depends on formality. 「私（わたくし）」 is very formal. Used both by men and women. 「私（わたし）」 is formal and neutral. But women can use it both for formal and informal situations. 「僕」 is informal used by men. 「俺」 is very informal used by men. In my opinion, Japanese learners should start by using 「私（わたし）」 You would sound polite and politeness is important for us. Then when you get intimate with Japanese friends, you may start thinking about other choices like 「僕」「俺」 in informal situations. We choose our pronouns which most suit for our personality. So if you are not sure what connotation they may have, it is better to stick to 「私（わたし）」

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