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Ok, first off, I'd suggest putting this in your blog section instead. It'll probably fit better there.
Now, as for the date....hmmm....flying glitches are a rather interesting idea. For instance, flying in the Tortuga mountain and such and just, I don't know, doing sight seeing or something from up there? There's also the decks of the taverns in Port Royal that you can get to, and you can have another sunset moment or something. That is, unless you both already know said flying glitches and how to get onto the decks and do them all the time, in which case it would probably be less "wow"-ful. Or, you know, just showing her any glitch in general that she doesn't know and would find interesting. If you're looking for ideas on those, go to the "Bugs and Barnacles" section of the forums.
Also, perhaps you could do some more sailing, trying to get a full load of royals for her to keep or something. I don't know, just kind of spitballing here.
Some people have favorite places they like to go on land for killing enemies, so if you know what her favorite place like that is, try thinking of something to do with that.
Ummm......yah. I think that's all I got for now. Hope it helps!
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