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Just curious, is your best friend a possible romance option? I've gotten both their lust and romance bars pretty high but they reject every time I try to make a move.

(+5)

They are, but it is tied to a specific event path.  There is a box marked Hints in your sidebar.  One of the hints is regarding that very thing.  It's titled 'The Best Friend'.  Follow it's recommendations & you will get there.