Throughout his life, Oliver has had many regrets. the main one always being his failure to keep Sara from harm. No matter what he does she always ends up the one suffering for his mistakes. It's something he can never escape from. His dreams are a constant reminder of how much he has failed the woman he loves.
After the fall of the mountain, Clarke and Wells set off into the forest and disappeared. Five years later Clarke shows up to Polis asking for Lexa for help as Azegda has attacked Floukru trapping them in their capital city. While Clarke gathers an army to save her people facing all the demons she tried to leave behind Luna and wells work to stop their home from falling Azegda.
What if Oliver ended up with the League of Assassins instead of Sara. And what if he left without permission to come back to save his city.
He lost her again. How does he keep losing her? Why can't he ever save her? Why does he have to keep losing the woman he loves more then anything.
After the events of New Year's Eve, the Doctor just needs to spend some time with her wife. to remember that the two of them are still alive.
"Hades, Irons... Will don't mean anything compared to your Ilona. That's why I want you to stay. You are the one thing in my life worth fighting for. I cant lose you like Will. Me and Gideon will end this. I love you.