Board Thread:Character Discussion/@comment-25850402-20160525123525/@comment-24674051-20160603170718

Here's how I see the Henry/Rumple relationship. In season 2, we have the revelation that Henry is Rumple's grandson (though Neal and Emma). and we have the reveal at the same time of the prophecy regarding the boy that will be Rumple's downfall. We are meant to believe, just as Rumple believes, that Henry is the boy of the prophesy. Rumple is at this point torn in his feelings, particularly given what had just happened with Belle. On one hand, Henry is family, and one characteristic that has been constant with Rumple is that he does care about his family (even when he has unusual ways of showing that care). But on the other hand, Rumple cares about Rumple, and anyone being his undoing is going to be treated harshly. And we saw that struggle, and the harsh side was close to winning before Rumple finally decided to help with the Operation Save Henry.

Season 3a is all about Rumple and his family issues, but at the heart of it, Rumple has put aside the prophecy and chosen family first. At this point, Rumple is at the height of his caring (and was briefly moved to the anti-hero column). skipping 3b, when Rumple was in bondage to Zelena, we see in season 4 that Rumple allows Henry to work in his shop, and I would say that if Rumple was aware of Regina and Henry's duplicity, Rumple still allowed it so that he could have some time with his Grandson. (Too bad the scenes that would have really shown Rumple's care were left on the editting floor). He did also include Henry in his escape plan during the spell of Shattered Sight. Then we get to the Season 4 Finale, in the AU, where Rumple attempts to Kill Henry, but I'll let that one slide since Rumple was not aware of Henry's status due to the forgetfulness caused by the AU.

Season 5 did not really have any real interaction between Rumple and Henry that I recall (Rumple was out of the picture in 5A for the most part, and separated from the group in 5B). So I don't think we can garner too much info here (except that Rumple was willing to leave Henry and everyone else in the UW at one point, but that was selfish Rumple). Again, until the Finale, where Henry Steals the Crystal and bugs out. I think had it been anyone other than Henry and Violet, Rumple would not have thought twice but would have ripped out the theif's heart and crushed it, or turned them into snail's and squished them under his boot. Instead, Rumple just put the 2 to sleep. The fact that he showed restraint could indicate that Rumple still respects Henry as family (and respects him enough to have restraint with his girlfriend), even when he doesn't agree with him. And recall the library fountain scene. Rumple made some comment about the boy having a few surprises.

So, did Rumple ever care? My opinion is that he did, and does care. Rumple just has very unusual ways of showing that care. And if Rumple ends up being the final villain of the series, Henry will end up being his undoing, because Henry is one of 3 people alive that Rumple would not harm (the other 2 being Belle, and the baby to come).