The word sleep is an affectionate word used to express future excitement or joy: five sleeps until Daddy comes home; three sleeps until my holiday.
Sleepy is a gentle word, whereas tired is a bit more serious. Depending on the situation, think about the mood you want to create with the words you use.
Sleepy is just a nice way of saying you look a little relaxed and calm, however, the word tired is a way of saying your eyes look droopy and you look absent.
Sometimes it is often a case of who is saying the word too. A male colleague would not say to his fellow male colleague that he looked sleepy, therefore, in this case, the word tired would be appropriate!
And, did you have a good sleep, is much nice than: are you still tired?
Tired is a word that has negative connotations which is why it can be harsh sometimes. Some people use it to express disappointment: I am tired of waiting for you to finish that. And of course it does matter how you say the word tired because a more positive tone, definitely helps. However, sleep or sleepy is hard to say in a negative way, even if you try!
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