Okay, so Will has a connection to a character from season one. I really thought it was going to be Marian but she wasn’t around in season one. Emma maybe? Granny? Red?
I’m pretty sure it’s Cinderella. We keep overlooking this because we–the people who watched WL–are already in the know that Ana is Cinderella’s step sister. But for viewers who did not watch WL, they won’t know that Will is Ashely’s step-brother-in-law. Also, the actress who plays ‘Ella was at the red carpet premiere, which felt odd given how little of her we see since S1.
I was just about to write the exact same thing! Ana must have gotten into some kind of trouble, and he seeks out Cinderella for help. That’s my theory.