Board Thread:Spoilers!/@comment-4877635-20160722094328/@comment-24674051-20160812183249

where did they say that the prince chose her stepsister?

In the conversation between Ana's (unnamed) mother and Anastasia, the only reference we get is that when Ana is preparing to go off, even after her mom chastises her, Her mom laments "Well, at least I have your sisters". By this, it is implied that Ana has at least 2 sisters, and I doubt that the mom (who is obviously suffering from a Cora complex without the power) would include any stepchildren in that count.

Now, I totally agree that randomly having Ashley be the Storybrooke person that Will runs into (and pickpockets), combined with the aforementioned dialogue, and the choice of Anastasia as a name, are probably not just coincidental. I just think that, possibly, Ana was the smarter of the Tremaine sisters. got tired of her Mom trying to vicariously live her life (and her attempt to grab royalty) through her, and left with the one person she loved. And that would be the Once twist on the Cinderella story. That's my headcanon, anyway, until they prove otherwise.