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How do you ask a group of people a singular question? If you are sitting with 2-3 people and you want to ask all of them about their day (they were not together and did different things), do you say "How were your days"? or do you keep it singular "How was your day?"

You/your can be both singular and plural so do we then keep it singular?

If you're posing another question to a group, should you ask it in the singular form? Also if people can provide different answers? Like "What do you want for dinner?"

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I'll say that this question is higly affected by the context.
To make it simple, i will suggest to use a word that refeers to everybody:
ex: Guys, how's your day going? or Girls, how was your day?

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How was your day? is a well-established expression and a way of asking a friend or friends whether they had a satisfying day. It's often just a way to introduce a conversation.

How were your days? makes no sense unless you are referring to a time spent, for example, at university or in some town or company. It's a way of referring to the time spent there.

How were your days with X travel company?

It doesn't matter what the exact size of the group concerned is. If there were several people, you might add ...you chaps / you guys or similar. Each person understands that the question is being directed at them. The same is true for the question about dinner, even if people want different things.

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How was your day?

“How was ... day?” does not change even when “your” refers to a plural “you”. Each person still has only one day being asked about.

It is usually clear from context when “you” is plural, but if not, we can use “you all” (or regional variants) to clarify it:

  • How was you all’s day? (standard)
  • How was y’all’s day?
  • How was you guys’ day?
  • How was you chaps’ day?
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In a group you could probably get away with just looking around at everyone as you ask, so it's clear you're not directing the question at one person specificially. Or you could do the same with language, start by explicitly addressing everyone with something like "so how about all of you, how was your day?"

There are a few suggestions about informal ways to change "your" into some explicitly plural form, so I'll just say: if you're being informal, you absolutely could say something like "so how were all your days?" because you're being playful with the language. So you might run across that kind of thing in some settings, especially online.

You get this kind of thing where "standard" English fails to convey enough information (is it "you" singular or "you" plural?) and people get creative! "So how were youse's days?"

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