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atp & enable me.

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Gil and Iri are going to be very... interesting here, because while he's aware of her existence and vaguely so of what she represents (I imagine Servants have a better handle on that sort of thing), he's also taken from a canon point from before the Grail's destruction and didn't get to see most of her personal shit up close.
Gil has also settled down considerably and while still kind of an asshole is unlikely to manipulate her to any truly nasty ends. They may very well end up getting along because he tends to bond well with 1) people who are kind and 2) people who are quietly wise and thus 1000% more willing to put up with his bullshit (see: Aslan). Oooor they could end up bickering terribly, because he has a very complicated relationship with Saber here and won't really tolerate the whiteknighting that's sure to happen.
Either way I do think he will end up encouraging her to seek out something for herself. He's bonded pretty hardcore with Diarmuid, so who knows?