"Will you be able to speak right away when you get back?"

He's not asking about the specific circumstances. Considering the sheer amount of things Inigo isn't explaining to anyone about his own circumstances (and it's a lot), he's not hypocritical enough here to go digging around for the details of anyone else's. If Sam might not want to talk about it, that's cool with him.

But he at least hopes the other can talk to his sister soon if he really wishes for it, that's why he can't help but ask.

"That'd be nice. It gives you something to look forward to."