Ishmael must have been alone after she became a Watcher/Observator, witnessing multiple birth and death of civilizations that fell to their own trials like hers almost did if she hadn't put it in a stasis. Maybe she had a few relations here and there but nothing too friendly too close, in order to not be submerged by the feeling of loss again.
She only watch those civilizations rise and fall in hope that one of them will win again those trials to save her own dimension, her friends, family and co-workers, even if there's not many of them left. Maybe she even helped a few individuals to go through the gate, making them watchers too and join the already mass of individuals that also have that role, restricted by rules because it was the only way for them to survive against the filtering of their dimensions.
So how much of a shock it must have been to her when Lee, with his limited grasp and understanding on time-travel, dimensions, alternative universes he learned not long ago in the Hetero-Tower with the help of multiple versions of himself that failed the trials of the Tower, Lee who only wants to protect those closest to him, to save them from the threat and futures he went through, and perhaps in a certain point of view, who's a reflection of Ishmael's owndesires and therefore should have accepted her offer, said no, they are waiting for me, thinking of SKK, Lucia, Liv and Murray because they are his family.
What do you think went through the head of the Merciful One when she heard his answer, denying powers and comprehension of their places in the universe that would take a long time for humans to control ? Yet she gives him her blessings, she lets him go, she doesn't force him to stay because a part of his answer, who he is to decide the fate of humanity alone, is correct. She had started to watch Gray Raven closely the moment Liv was on Empyrea but she watches them closer after the Hyperreal user defies her expectations.
Then she assist to a third (Lucia) and fourth round (SKK) of Gray Raven trying to find a future where they are together or their loved ones lives on, the last one actually going through the door with her help but chose to go back in time instead of stopping the time of its world, traveling to other dimensions with her to find a solution elsewhere, and finally giving her company and someone that can understand her other than Gestalt, which would have been safer for Skk or Lee if he had chosen to accept her offer.
But no they are stubborn, refusing to sit and watch idly, doing nothing while other are fighting for their futures because you obtain nothing if you stay passive. So she finally takes a stand too, even if she has to pay a great price for it.
And maybe, maybe she is starting to fall slowly but hard for those two that showed her the way, reigniting feelings she had long since foregone and forgotten because they are useless to her current situation. And as a raven from another dimension and civilization, she can't let them do everything, she has to show she is a raven they can trust.
TL:DR Leeshmael, skkshmael, leeskk and leeshmaelskk are living rent free in my brain, rotting inside of it and this is my thesis/analysis on them, with a pinch of raven courting behavior on Ishmael's side since her civilization has apparently raven in its name.
