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.
While Anakin Skywalker is ultimately reawakened by the love of his son, Darth Vader is relentless in the disdain and loathing he holds towards his enemies - none more than Obi-Wan, who struck him down on Mustafar, leading to Palpatine rebuilding him as his cyborg servant.
Darth Vader showed no emotion at all when he killed Obi-Wan Kenobi. If you watch the scene carefully, you will see Kenobi pausing. He was letting Vader kill him. Whether Vader knew this at the time, or discovered it later, is an open question.
The short answer is yes, without a doubt, Vader regretted becoming a cybernetic monstrosity.
Yes, when Darth Vader turned back to Anakin Skywalker and sacrifice himself to save his son, he dies and Obi-Wan uses the force to connect with Anakin's spirit. In that time Anakin apologizes to Obi-Wan, desperately asking him to forgive him for everything he has done to him and everybody over the years.
Even after his brutal scorching in the fires of Mustafar, sand remained the only natural phenomenon that Vader feared. To him, sand was a reminder that he'd failed to save his mother or Padme from death.
Obi-Wan apologizes for what he did to Anakin, but Vader assures him that he killed Anakin, not Obi-Wan. He then goes on to proclaim that he will destroy Obi-Wan in the same way. Resigned to the fact that his friend is truly gone, Obi-Wan walks away from Vader, calling him "Darth" for the first time.
Darth Vader hated Obi-Wan Kenobi because he hated himself. This started when he thought that Kenobi was the one that poisoned Padmé into turning against Anakin when he turned to the dark side.
Of course, Obi-Wan didn't finish Anakin off ten years ago on Mustafar because he didn't want to be the one to strike the killing blow on a man that he loved like a brother.
The answer is seeming, simple: Obi-Wan's self-imposed isolation also includes a news blackout. Not only does he not spread information about himself around, but, he also doesn't appear to take in any new information about what's going on in the galaxy.
Many have taken to the Internet to suggest that if it was really killing Kenobi that Vader was after, he simply could have brushed away the fire that followed to thwart his escape. And that is true. However, Vader is not just looking to kill Kenobi. He wants to make him suffer.
learn how Vader felt upon striking down Kenobi. from Yoda, rather than feeling relief. or vindication at finally destroying his old master, Vader, or rather Anakin, was instead. overwhelmed with utter loneliness and sorrow, having killed one of his last. remaining links to his former life.
He betrays his closest friend in hopes that, somehow, he can save others. Ultimately, the tragedy found in Anakin's willingness to rebrand himself as Darth Vader is that he betrayed himself. His forfeit of himself surrendered the capability of becoming great without having to concede to the Dark Side.
First and foremost, Obi-Wan didn't want to have to confront and try to kill Anakin, we see this all the way until their final conflict in their duel where Obi-Wan pleads with Anakin to not make him do what he knows he'll have to do if Anakin tries to attack from the low-ground.
Anakin Skywalker: [shouts] I HATE YOU! Obi-Wan: You were my brother, Anakin! I loved you!
But in a strange moment of comfort, Darth Vader took much of the weight off Obi-Wan's shoulders. He told him, “I'm not your failure, Obi-Wan. You didn't kill Anakin Skywalker. I did.” We saw later in the original trilogy, on some level Ben still believed he bore some responsibility.
She also knows Obi-Wan, and she knows him well. Her holographic plea for help, already iconic, will never be the same. She knows Obi-Wan's real name as well as his alias of “Ben.” When Luke comes barging into her cell and says, “I'm here with Ben Kenobi,” Leia jumps off the bunk in an instant.
Visions of Obi-Wan. The comic opens during the last moments of Revenge of the Sith, recreating the well-memed instance when a despondent, freshly-armored Vader cries out with a drawling “nooooooo” over how much he's lost.
Theory 1: Leia Doesn't Remember Ben Is Obi-Wan
Throughout her encounters with Kenobi in the series, he refers to himself as Ben. The most straightforward explanation would be that Leia knows the person who rescued her is Ben, and never connected the dots that Ben is actually Obi-Wan.
Grand Moff Tarkin. Although his status in the Empire may rival or even surpass Vader's own, Vader nonetheless respected Tarkin a lot, for many reasons. He thought Tarkin as one of the more competent and dedicated Imperial officers, with a sense of honor and being able to inspire loyalty in his subordinates.
In Star Wars: Episode III - Revenge of the Sith, Darth Vader slaughtered Younglings to cement his position as Palpatine's apprentice - but he was still haunted by this after The Empire Strikes Back.
Before Anakin Skywalker became Darth Vader, R2 was Anakin's astromech and a good friend. Anakin and R2 first met when Anakin was 10 years old on Tatooine. During the Clone Wars, R2 went missing and Anakin went to great lengths to get him back.