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Sorry, but let's be consequent - if there is only "your girlfriend" accepted, so why the only confirmed translation for "아들은 아빠에게 편지를 보내줄 거야" is "the dad", not "his dad" (or anyone else's)? I know it's more natural here but still, you can meet someone's (eg. mine, his) girlfriend as well.
The problem here is in English, by putting the time expression at the beginning of the sentence, you are shifting the focus on the time.
Your sentence could be interpreted as: "Speaking of tomorrow, [...]"
--> 내일은 네 여자 친구를 만날 거예요?
The expectation is to learn more about the listener's activities 'tomorrow' besides "whether or not to meet the girlfriend".
As far as DLG Korean sentence stands, the emphasis is on the Listener and the possibility of him seeing his girlfriend.
Hope I am not confusing you further.