Actually, the mention of Chucky was at the new comic-con, I think. Just like they joked that Goofy was Henry’s father. 🙂
I think Emma also did something illegal–she certainly has a good amount of knowledge when it comes to crimes and how to track people. Granted that was her job, but it could have started from even younger. Also, she gave Henry away for a reason–she must have thought that not only would he be more comfortable financially with someone, but that she would not be a good mother–in the second episode, Emma states that she would not be a good mother to Regina.
From the photos of a young Emma with Neal, they both could seem like young (well Emma is young) thiefs enjoying each others company.
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