Like, seriously, I have had a few people talk about how my fiancé wasn’t conventionally attractive, but he’s attractive to me :)
Plus, he’s good to me, and I don’t date for looks. I’ve had conventionally attractive exes too who have been horrible people, so…
I’m not straw-manning any more than you were, given the information at available at the time. and it’s perfectly possible to have commented on someone’s unattractiveness in an empathetic way.
In this case it sounds like neither their friend nor their father did, and I personally wouldn’t because it seems like a minefield, but I have seen cleverer friends and family navigate those minefields.