I really doubt how much remorse Chuck actually felt towards Jenny after using her in his pathetic wargames with Blair in Season 4
Chuck really is a trash excuse for a human being who seems to show remorse for his actions but goes back to his toxic ways after 2 episodes. He starts this season by coming back & apologising to Lily, saying how he was hurting & didn't mean to use Jenny's pain. I do think he felt remorse for his actions on some level, but after saying that for him to just use Jenny again as a dummy to make her feel the wrath of Blair is such a heartless, cruel thing to do to a person u've caused so much pain in the recent past.
To those who don't remember, Blair & Chuck r once again battling each other in their pathetic loser games, & He gets Jenny an interview at Parsons, knowing Blair would lose her marbles seeing Jenny return.He then steals her design book, forcing Jenny to collect it from his hotel, in the process Jenny getting spotted at Chuck's hotel & Blair losing her sh*t. I'm not even going to get into how pathetic Blair is in this entire episode, After a while her cruelty towards Jenny stopped being "entertaining" & just became painful to watch. But for Chuck to apologise to Jenny, for both the Pilot & the Season 3 finale incidents, apologising to Rufus & Lily only a few eps before, just to go back to his default settings & use her like this again really made me doubt the extent of his growth & remorse.
I do remember the scene with Rufus where he said he would never even imagine to hurt Jenny ever again, yet here we were. I've always felt his character arc is overrated by his fans(tho that's another topic for another day),but he doesn't actually stop being toxic even in the later seasons. I at least expected him to lay off of Jenny after their history, but I guess I gave him too much credit. Silly me.