The life of hunting was dreadful and lonely. Younger you and the Winchesters had no idea what was in store for the future. If only you could have gone back in time and warned one another, about the life they were going to live.
It wasn't all bad. You and Dean had started dating, and Sammy had Eileen who was a great addition to the family, along with Castiel and Jack. Life could have been worse if you hadn't had one another.
Dean died... Finding out from a crushed Sammy, it had killed you to see him this way, you both were heartbroken. But eventually, Sam moved on... Started a new life by welcoming a child with Eileen, Dean Jr who was the most adorable kid ever.
You never moved on, you kept trying to bring him back. Nothing ever worked. Jack ignored your prayers and questions, Castiel told you why and whatnot.
One day you woke up... Not in pain anymore, You heard the classic rock music, and a familiar voice humming. "Heya Sweetheart, I missed you" Dean grinned as he drove the Impala.