Both Prince Charming and Jack had siblings that they were unaware of until their adulthood. Prince Charming’s twin brother, the born prince, was separated from him at birth by Rumpelstiltskin. Jack’s father had an affair with another woman, resulting in Jack’s half-sister Claire, coincidently one of the other survivors of the plane crash.
Both Prince Charming and Jack had difficulties in making up their mind on who they loved. David Noland had an affair with Mary Margaret Blanchard, while he was still technically married to Kathryn. Jack Shepard, throughout his time on the Island, debated whether he loved Kate Austen or Juliet.
Despite being the handsome leaders who came to save the day, both characters could be extremely stubborn and controlling. Prince Charming prevented Snow White from killing her nemesis the Evil Queen, but was fine with ordering the queen's execution. Jack was the last of the survivors to realize the truth behind the Island because he could not rationalize it.
The very obvious connection between these natural born leaders was the fact that they both had similar names. Prince Charming was referred to by King George as the “shepherd,” while Jack’s last name was Shepard.
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