I dont know what you guys use as reference, but i have another sort of view. But first, a disclaimer:
I assume we're all agreeing on the fact that tarot is like a machine that works on SUBJECTIVITY, arent we? And thus, personal view is the only thing we can give, is this right?
Then, another quick disclaimer:
I THINK that meaning should be given by *you* and nobody else. It's ok to say "hey, i need ideas to read 5, or cups, or 5 of cups, because i'm not getting anything from it". It's not -in my view- ok to say "hey, read this for me, will ya ;D?". Now, you clearly are stating that you already read it for yourself, and thus you're looking for opinions, so, one of the things i'll say is that if that's what you feel, then THAT'S WHAT IT IS
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Finally, the actual reply:
I read 5 as "change intended to move towards something hidden", and cups as "intelligence, emotions, feelings, senses".
So, a 5 of cups for somebody's feelings would be something along the lines of "he's starting to see or percieve something from you that he has never seen before, and this is charming him, and making him want to discover that new, fresh thing".
It'd be something like he's seeing you in a new way, and he's loving it
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John