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いってらっしゃい itte rasshai
Off you go — and come back safe.
What does itte rasshai mean?
The reply to itte kimasu, said at the door every morning. It quietly assumes you are coming home again, which is the nicest part of it.
Example
いってらっしゃい、傘は持った?
Have a good day — did you take an umbrella?
Vibe
Who you can say this to, and how it lands.
Safe to use Fine in ordinary conversation.
The story behind itte rasshai
Unfold the contraction and you get itte irasshai, go and come back, with the honorific verb doing double duty for going and returning. The reply to itte kimasu is therefore not goodbye at all. It is an instruction to return, issued every morning at every front door.
Once you notice that, the phrase turns quietly enormous. It builds the round trip into the farewell, so parents say it to children heading to school, shop staff call it after departing customers, and it can wobble a person leaving for something genuinely uncertain. Translation flattens it into have a good day, which is friendly, sensible and missing the whole point.