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What's the natural way to ask a friend to tell me when he wakes up today? I was thinking about: "Let me know when you wake up", but I have a doubt if it shouldn't be: "Let me know when you're awake", or even "Let me know when you're waking up".

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It depends on whether you want a response now or in the future. Let's assume your friend John is waking up tomorrow morning.

Let me know when you're awake.

Effectively "please contact me in the morning". The most natural and conversational. When John wakes up and is ready to talk to you, he'll message you. You could also use "up" instead of "awake"; you can be "awake" and in bed, which may be relevant to your plans with John.

Let me know when you wake up.

Usually means the same as the above.

Let me know when you normally wake up.

This is an implied question about future behavior. What time does John set his alarm clock to? "... when you plan to wake up." or "... when you will be up." are other common forms of asking about John's future plans. "Let me know" often implies a delayed response to the question, but the response is expected to come before the event you're asking about.

When are you waking up (tomorrow)?

A direct question about the future. Most relevant when you're making plans for breakfast and you're trying to coordinate.

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