In the past lifetimes, Jackson only came close to Fil once. The rest, he simply tried to help her from the sidelines. After all, meeting her in all those twenty-one lifetimes were all different stages in her life.
Some, he would meet her when she was just a young toddler. Other times, she was already at the last straw of her life. If he met her as a young adult, she was either too crazy to even make any relationship or already happily married to someone else.
Only in this lifetime was he given a chance to be with her, to tell her his vows, to love her, and to be loved back by her. It was not a stretch to say they finally aligned. In this lifetime, they could continue the story that had ended in tragedy.
But alas, with Jackson losing his senses, he couldn't help but wonder.