Part of being a Grey's fan is being up for anything, even shipping step-siblings. While Jackson and Maggie find their footing in season 14, their relationship has been more on the rocks recently. Jackson goes MIA to find himself for a while, only after telling Maggie he loves her. When he comes back, she becomes jealous over messages on his phone from other women. Still, with Richard's recent bar fight and Catherine's diagnosis, the couple will definitely need to get it together. But if they are able to go through this, I can only imagine their relationship growing stronger.