This is definatly one area of the teaching that is hard to swallow. I think the attachment to "dear ones" is so strong because it lies at the heart of what makes us human - it's what bonds our communities and families together and to abandon that is to reject something seems intimately connected with being a human. It's something we've known (if we are lucky) from the day we are born and it has helped keep us alive and well. It's a scary thought, at least for me, that we must give this attachment up.
But to awaken is to go beyond being "human" - "remember me as awakened".
I think part of the problem for many is in a lack of seeing this attachment as a clinging that leads to suffering, we'd rather gloss over either the suffering part or the attachment part, as your Catholic friend seems to have done, Sam. That should be fixed by contemplation of the first and second (third?) truths, I would think.
"If beings knew, as I know, the results of giving & sharing, they would not eat without having given, nor would the stain of miserliness overcome their minds. Even if it were their last bite, their last mouthful, they would not eat without having shared."