He couldn't bring himself to kill Darth Vader, however, because he continues to associate him with the Anakin he trained as a boy. This is also the exact reason why Obi-Wan didn't kill Anakin on Mustafar despite the opportunity a decade earlier in Star Wars: Episode III - Revenge of the Sith.
Obi-Wan knew it was only a matter of time. So, he made the difficult decision to use his learnings and become one with the force, rather than let Vader decapitate him.
Did Darth Vader ever regret killing Obi-Wan Kenobi in Canon or EU? He does. Right at the end. With Luke crying over him and Vader sensing his anguish and pain he had inflicted on all those who had cared for him.
Originally Answered: Why did Obi-Wan Kenobi let Darth Vader defeat him? Because he wanted Luke the get the Hell out of there, and he knew Luke wasn't going to leave his mentor behind if there was a chance to save him.
He slays Sidious and returns to Obi-Wan, begging for atonement by execution, only to be met with true forgiveness instead. But just as this fantasy Obi-Wan refuses to strike his former friend down, Vader refuses to turn his back on the dark.
Anakin admits to Obi-Wan that he has been arrogant and unappreciative of his training, and apologizes to his master. Obi-Wan assures Anakin that he is proud of him, telling him that he has become a "far greater Jedi than I could ever hope to be."
Darth Vader only learned he had a daughter in Return of the Jedi - but there's no evidence he realized she was Leia before his death and redemption.
The first reason is that A New Hope was filmed during the 1977, when the visual effects weren't nearly as good. Lucas was already filming on a short budget, due to the studio executives not trusting him with huge sums of money. The lightsabers were filmed using lots of wood, foil, and pipes.
but how many total Jedi did he kill over the years? in canon, we can confirm that Vader killed at. least 22 Jedi during Operation Nightfall alone. most of these that we actually see were younglings, but he did kill several Masters, with the most notable being Shaq, Ti and Syndralic.
Anakin does not have even the slightest bit of remorse. By the end, he feels nothing but anger. Although he feels regret for killing Padme, he still helps the evil Emperor. The film ends with Anakins standing side by side with the man on whose behalf he has committed all his crimes.
As he turned to the Dark Side and became Darth Vader, Anakin came to hate Obi-Wan, but never stopped respecting him. In the end, it was Vader who would take Obi-Wan's life, but it was Obi-Wan who would set up the path for Anakin to be redeemed.
Vader responded “I am not your failure, Obi-Wan. You didn't kill Anakin Skywalker. I did.” This allows Obi-Wan to finally accept that Anakin is truly gone and that there was nothing he could have realistically done to save him.
Arguably, most Star Wars plot points revolve around characters simply not knowing something, very often about their family history. But, on top of all of that, the biggest reason Obi-Wan doesn't know Anakin is alive is that the last time he saw Anakin Skywalker in Revenge of the Sith, Ben literally left him for dead.
Darth Vader hates Obi-Wan, not because he blames him for his fall to the Dark Side, but because he turned Padmé against him and destroyed his body.
Over the years since the Youngling massacre, and even sometime before, Darth Vader has regretted killing the Younglings, recognizing that it was the most terrible thing he had ever done.
Darth Sidious was always stronger than Vader, which is why he ruled over him for almost 20 years and turned him into the Sith Lord he was.
Reva knows that Anakin Skywalker is Darth Vader because she was one of his targets—a child—during the Order 66 killings that took place during the events of Star Wars Episode III: Revenge of the Sith.
Darth Vader Likely Hates Padmé
In other words, Vader could only be in love with the Padmé before she betrayed him and hates her for not accepting what he became. In 2017's Darth Vader series, the eponymous fallen Jedi goes out of his way to deform Padmé's personal shuttle he later acquires.
The real answer is: When the original trilogy was written and filmed, Anakin Skywalker was not the creator of C3PO. There was no consideration given to who Vader would recognize, because there was no reason for Vader to recognize the droid, at all.
Sort of. He's filled with regret, but didn't care much about the Jedi per se, because they never showed much care for him and couldn't help him save his wife and their unborn child. Of course, he HATED Palpatine, because he enabled him to be able to save her, but then set him up to be the instrument of her death.
The short answer is yes, without a doubt, Vader regretted becoming a cybernetic monstrosity. First, there's the constant pain and discomfort from his suit. Worse, however, is the psychological pain. Vader destroyed everything he had ever known for a chance to save Padme.
Before he discovered Vader had survived Mustafar, Obi-wan lived with the regret of killing his son, brother and best friend. After, he regretted not killing him and wondered if he had only made things worse by pushing Anakin further into dark side and Palpatine's arms.