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Rewatching episode II of Star Wars, it's very clear that Obi Wan knows that Anakin has feelings for Padme...such as when Anakin admits he's bothered that she's back in his life...or when Padme falls out of the troop transport and he yells at Anakin to not throw his career away for her

My question is, as Anakin's master shouldn't he have done something about this before Anakin was promoted to Jedi Knight instead of allowing this to continue and leading Anakin to the dark side?

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    Because he couldn't control himself from falling in love.. What was the name of Mandalore's queen, again? – Baby Yoda Sep 28 '14 at 16:05
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    @SachinShekhar - did you mean Satine Kryze? – DVK-on-Ahch-To Sep 28 '14 at 17:47
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    @SachinShekhar - she wasn't the only one. There was also Cerasi that caused him to renounce his Padawanship with Qui-Gon and leave Jedi. – DVK-on-Ahch-To Sep 28 '14 at 17:58
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    ^ The above information by @DVK is from Jedi Apprentice - The Defenders of The Dead and Jedi Apprentice - The Uncertain Path, in case anyone is interested. – TylerH Sep 29 '14 at 18:08
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    @TylerH - yeah, makes me wonder if whoever was writing that series of books had major unresolved romantic issues. – DVK-on-Ahch-To Sep 29 '14 at 20:25
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The official novelisation gives some insight into Obi-Wan's thought process. In short, at the start of Episode II he's far too distracted by the bigger picture to concentrate on what he views as an adolescent crush and he certainly doesn't think that Padmé has any romantic interest in Anakin:

The eagerness with which the Padawan had embraced his new duty set off warning bells in Obi-Wan’s head, but he had allowed the mission to go forth anyway, mostly because he knew that he’d be too busy following the leads he hoped he could garner here, uncovering the source of Amidala’s troubles.

By the time he's noticed what's going on, he raises the issue with Mace Windu and gets slapped down. He considers pushing the matter further but comes to the conclusion that Anakin's lack of emotional detachment is a form of test that he'll simply have to overcome. Note that he doesn't even consider the alternative:

“But he still has much to learn. His skills have made him… well-” Obi-Wan paused, trying to walk that delicate line. “-arrogant. I realize now what you and Master Yoda knew from the beginning. The boy was too old to start the training, and…”

“He has a… an emotional connection with her. It’s been there since he was a boy. Now he’s confused, and distracted.” As he spoke, Obi-Wan started toward his star fighter. He climbed up the cockpit ladder and into his seat.

“So you have already stated,” Mace reminded. “And your concerns were weighed properly, and did not change the decision of the Council. Obi-Wan, you must have faith that Anakin will take the right path.” It made sense, of course. If Anakin was to become a great leader, a creature of prophecy, then surely his character tests must be passed. Anakin was waging one of those tests right now, Obi-Wan knew, off in seclusion on a distant planet with a woman whom he loved too deeply. He had to be strong enough to pass that test; Obi-Wan just hoped that Anakin recognized the trial for what it was.

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    That still sounds like a lot of hand waving (why didn't Obi Wan ensure that Anakin had "passed the test"), but I guess that's the canon's addressing of the issue. I'll accept this answer – user1203054 Sep 29 '14 at 20:27
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    @user1203054 - Don't blame me. I didn't write the damn thing. If I had, it would have been 2 hours of nothing but light saber battles and padmé nudity – Valorum Sep 29 '14 at 20:39
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    I know, I was just trying to say that Star Wars is not known for the quality of its writing :) – user1203054 Sep 29 '14 at 20:42
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    The sole line in my film would be "That's not my lightsaber"... – Valorum Sep 29 '14 at 20:43
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Obi-Wan himself has in the past felt the stirrings of affection and love for someone. And in fact, he lost the object of his affection. It may have been a painful situation in itself to deal with and was hoping that Anakin came to his senses.

And as others have stated, Anakin was being watched by the Council to see what he would do and handle certain situations. This of course did not prepare the Jedi for his eventual fall, but part of that was due to the designs of the Chancellor in influencing Anakin and deceiving the Jedi Council.

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    The point about Obi-Wan and Satine doesn't quite work in relation to the events in the question since Obi-Wan and Satine's relationship was during the Clone Wars. The events referred to in the question happened prior. – phantom42 Nov 25 '14 at 18:26

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