11. Fighting Asajj Ventress
During the Clone Wars, Obi-Wan Kenobi ended up fighting many non-sith Dark Side dwellers and Asajj Ventress was one of those. She was kind of a semi-apprentice to Count Dooku and learned most of her skills from him. Ventress wielded a double pair of curved-handled lightsabers and was a fierce combatant.
She was utilized by Dooku in the plot to kidnap Jabba’s son and turn the Hutts against the Republic. Obi-Wan confronted her and an exciting lightsaber duel ensued. During this duel, Obi-Wan is clearly toying with the young dark force user. He almost flirts with her and calls her darling, as they cross sabers. He seems to be sort of training her as the fight continues and is never once concerned he may come out on the wrong side of this battle.
Obi-Wan was never as arrogant as Anakin was in the prequels, but this is about as close as we see to him being overconfident. That being said, this battle was not only a great duel but showed a more light-hearted side of Obi-Wan as he realized his skill in the Force was much stronger than that of Ventress.
10. Training Luke
When Obi-Wan and Luke secure passage to Alderaan aboard the Millenium Falcon, they get a moment to sit. Obi-Wan uses this moment to begin Luke’s Jedi training. He uses the remote and has Luke deflect the blasts with his lightsaber. When Luke begins to struggle and takes a few blasts to the buttocks, Obi-Wan instructs him to lower the blast shield so he can’t see.
Luke eventually does and is shocked to find out that he can sense the blasts without seeing them. This scene is one of the first examples we get in Star Wars of how the Force works. We also get to see Obi-Wan in that teacher/mentor role and how he calmly deals with his new apprentice and his frustration with dealing with the remote.