[General] Once you're in town, feel free to be my guest.

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Silverobama

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Chris is in Costa Rica now. He's a very generous man and a friend of mine. He sent some red packets (money in it) to my friends online (an app with a system for people to send red packets). I appreciate his generosity and I know he'll come back to my city one day. I said to him "Once you're in town, feel free to be my guest".

The intended meaning is "Once when you're in Chongqing, I'll treat you on everything to return your generosity".

Is my italic sentence natural?
 

emsr2d2

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Chris is in Costa Rica now. He's a very generous man and a friend of mine. He sent some red packets (there was money in [strike]it[/strike] them) to my friends online (there is an app [STRIKE]with a system[/STRIKE] for people to send red packets). I appreciate his generosity and I know he'll come back to my city one day. I said to him "Once you're in town, feel free to be my guest".

The intended meaning is "Once when you're in Chongqing, I'll treat you [STRIKE]on[/STRIKE] to everything to return your generosity".

Is my italic sentence natural?

Note my corrections above.

Don't use "once" there unless you know that a) he's coming back and b) the date he's coming back. Say "Next time you're here, everything's on me". Be careful what you offer though - saying that you want to treat him to everything means you'll be paying for his hotel, all his meals, all his excursions, potentially even his air fare!

Note that "be my guest" would be taken to mean that he can come and stay at your house for the duration of his visit. Again, be careful what you offer. You probably want to be clearer. "Next time you're here, I'll treat you to a slap-up meal" or something similar.
 

Silverobama

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I'm grateful for your detailed explanation. He did tell me he'll come back one day but we don't know when because China is still closing its border.

Much appreciated! I've learned a lot from this post!
 

emsr2d2

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I'm grateful for your detailed explanation. He did tell me he'll come back one day but we don't know when because China is still closing its border.

Then you can't use "once" there. Note that I said you had to know both a) and b). At some point in the future, when you get a message from him saying "I've booked my flight! I'll be arriving in Chongqing on May 23rd", then you can say "Great! Once you're here, I'm taking you out for a huge meal!"
 

GoesStation

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I'm grateful for your detailed explanation. He did tell me he'll come back one day but we don't know when because China's border is still [STRIKE]closing its border[/STRIKE] closed.
See above.
 

Skrej

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"If you ever make it to (your city), dinner and drinks (or whatever you plan on paying for) are on me/are my treat."
 
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