2) In-between the events of “The Crocodile”. When Killian and Milah were sailing the oceans together. That’s roughly 7 years or so to take into account. Baelfire was probably around 7 when she left, but 14 when Rumple lost him. They would have to get Rachel Shelley back as Milah, which may not be all that difficult. I honestly would be intrigued on exploring that time period. We only saw the beginning and end of their relationship, after all.