Sure, it was a hologram, but I believe -- and I think Star Trek did a nice job of showing this -- the holodeck is based on reality. When the holodeck features literary characters, it depicts them incredibly well. For example, Moriarty acts as the supreme super-villian.
Of all the available examples (Newton, Freud, Hawking, Samuel Clemens, Leonardo, Leah Brahms etc.) you chose the fictional character played by the guy from "The Nanny!" Nice going
On T'Pol and whether she thought about Trip or not, by the nature of her conversation with Riker, I got the impression she hadn't.
...And then you attempt to prove a point by referring to one of the conversations that
we know for a fact never took place. Holograms are no more than imitations of real people, empty shells, that's it. They imitate the personalities of real people, but they don't know what those people really had on their minds, how they felt...
Real life Leah Brahms for example, turned out to be almost nothing like the one Geordi 'played with' (though he's the one to blame for that, making her his love doll and all).
And then, of course, there's Moriarty, who basically achieved awareness by accident, and transcended the character on which he was based...
Wait... Are we discussing TATV again? That
"Spock's Brain Award" winning classic? Oh brother...