Sam had Jessica and was going to Stanford for law. Then their dad went missing. Dean came back for Sam. Then when they got back? Jessica died. And Sam and Dean went back on the road hunting again. Dean at 26 when they start hunting again Sam at 22. The brothers carry on hunting. Sam has always thought Dean was a womanizer. But in reality? Dean flirts to keep up an act that Sam expects. But in reality? Dean got married when he was 23 and has a wife and two kids in a cabin in the woods in Alpena, Michigan. He gets caught up in the work, and he texts and calls when Sam isn’t looking. But three years pass before Dean finally has enough. They’re in Wisconsin for a job and Dean just cannot be away from home anymore. He finally comes home. Dean doesn’t tell Sam where they’re going. Just that he needs to go