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For example, if I make a Secret Pal on Day 1 and collect 30 flags from them that day, can I then go to the same Secret Pal on Day 2 and collect whatever amount of flags they previously collected in Day 2?

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Does this answer your question?
"Occasionally, a Secret Pal will also gift the player with a number of flags they have collected (ranging from 1 to 30) the first time the player speaks to them."
https://bulbapedia.bulbagarden.net/wiki/Secret_Base#Secret_Pals
It would be great if a source specifically stated that the Secret Pal only gifts flags the first time they are spoken to, never any other day. However, if nothing like that exists, that Bulbapedia quote is fine.

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