[ He can't say he's entirely sure what to think about it; whether he should be pleased or concerned. Data won't be compromised by her, he knows, but even if he is, with the lessons they've learned in the past, with Lore and Dr. Seung, with the Borg Queen, both from Data's perspective and Will's own, he doubts any easy mistakes will be made as a result of their overlooking the dangers.
And he'd...liked Seven. She was articulate, pleasant, respectful--maybe a little too Borg, but he could get over it, at least on the surface.
Riker didn't like himself for judging her by her demeanor and outward appearances. He wasn't that kind of man, really and truly desired not to be, but war and death and loss had hardened him, and mending those bridges was a personal challenge he meant to overcome, needed to overcome. He'd been the first Starfleet officer to serve on a Klingon ship, challenged himself just like this before, and he meant to do so again.
Human xenophobia against those returned from the Collective, as it was with holograms, Cardassians, Romulans -as it still was in many places even for Data - was a deplorable quality in any Starfleet officer. But more importantly, it was a quality he found deplorable in himself. ]
I know that it's a gentleman's prerogative never to kiss and tell, but would you mind...I mean, can I ask how that's going? [ He doesn't want to say 'as your commanding officer', he'd much rather know as a friend. ]