do you think henry ever felt regret for killing anne? also, what do you think drove him to do it in the first place?

This is…a bit heavy for a Wednesday…

It’s hard to know because a lot of the evidence of Anne’s existence (portraits, etc.) was destroyed; likely most of this was done under his command (although we don’t have access to the official records for this, as such), but strangely enough not all of it was? Their initials are still over the fireplace in the Presence Chamber of St. James Palace, for instance. We could chalk this up to an accidental oversight, but as Henry had this palace remodeled in 1544, it would seem he had ample opportunity to take them down and never asked the renovators to do so. 

Anne was referred to as the “late Queen” in English warrants/records of Henry VIII’s reign as early as August 1536. This kind of begs the question of ‘how’–their marriage was annulled by Cranmer in May. If her marriage to Henry was never valid, then how was she the Queen? 

I’ve talked more about possible explanations here; also about items from her inventory he bought. 

The scene alluding to this in Tudors, while of course fictional, is interesting…if the figures of Anne and Elizabeth are not, in fact, ghosts, but rather images from his subconscious, Anne’s “I was innocent, all the accusations against me were false” is actually just what Henry’s known all along (or, perhaps, finally knows). And when he says he wishes he could love Elizabeth more, but from “time to time she reminds me of you, and what you did to me”, Anne’s “I did nothing to you” (and then the rest above) would indicate that his distance from Elizabeth stems not so much that Elizabeth reminds him of Anne, but more from how Elizabeth reminds him of his own guilt.

Idk, I just mention the scene because I admire its complexity and I think your question…has no simple answers, really. 

So…did he ever feel regret? We’ll never know. I tend to think that he did, but that at the same time, if we ever brought him back from the dead to ask him “Was it all worth it?” (’it’ being…well, what happened to Anne, and all of the best and the worst of his reign) his answer would be “yes”. 

As for The Million Dollar Tudor Question (why/how could he do it/ how did this all unfold?); I’ve touched on it in essay-length asks:

here

and here.

*edited version