Board Thread:General Discussion/@comment-24589671-20141222210529/@comment-24674051-20150112181403

Well, we know that David has a history with Maleficent. We saw that in season 1. Now, if Snow also has one, it would not surprise me if it was with Cruella. Maybe (wishful thinking here) something involving Snow and Red with Cruella.

In thinking about it, Maleficent has crossed paths (at least) with just about every major, and even most of the semi-major, characters.

Ursula has been quiet for quite some time, except for Rumple and Belle, and possibly briefly with Regina (from the end of "Ariel"), at least if you believe Ariel's comment regarding Ursula. So, any other interaction is most likely going to have to occur farther in the past, which limits it to Rumple and Killian.

Cruella is somewhat of a wildcard, though. We know nothing, really, about her past. Based on the underlying story, She will have a past with Pongo, which leads to a potential background with Jiminy.

Back to the topic, It makes the most sense that Ursula would have had interactions with Killian in the Past, probably before he departed to Neverland, and maybe even before he became a pirate. But I would at least leave the door open for other twists, since we know that A & E love to do that type of thing.