"How was your night?" could mean, e.g.: - Did you have a good evening; did you enjoy the film you went to see? - Did you have a good time with your new 'date'. - Did you sleep well?/ Did you have a peaceful night. - Did many bombs drop last night to disturb your sleep? As you said, it depends on the context, but it could refer to either your activities during the evening of the day before, or the night (the time when you usually sleep).

Hi Olai, You are correct in thinking that the question "how was your night" is usually something that gets asked after someone has gone out for the night (e.g. to a party; to a bar; to a concert...). I suppose it could be asked if you spent the night with a (sexual) partner, in a sort of euphemistic way (a euphemism is an indirect way of asking about something rude, explicit, or unpleasant). For asking about sleep or rest, we probably wouldn't use this phrase. Instead, you could say something like: "Did you have a good sleep?". I suppose an exception might be if there is a particular reason to think that someone's sleep might have been disturbed (e.g. by a newborn baby; noisy neighbours; jetlag...). You are right in thinking that context is everything :) I hope you find this helpful.

I agree with Charlie that it can mean all the things he listed in the right context. Specifically for asking about how a sick person slept, I'd be more likely to follow it up with a more specific question, "How was your night? Were you able to get some sleep?"

How was your night and your day today?

Personally, I don’t think it’s a good or natural way to ask any of the things you mention. Better are: How was your evening? How did you sleep? Did you sleep together? How was it? Perhaps I’d use it in a context where there was something specific understood. For example, if I worked the night shift my morning replacement could ask me that. (We would both understand that I work ‘the night’)