Sammy was wrong in thinking Dean didn't want all the same things that he did. Well, maybe not the high class education and the high paying job. Because Dean liked working with his hands, he was good at doing things with them, and he didn't need a whole lot to be happy.
Everything else though- the home, the significant other, kids… a family that was tangible and his to come home to. Dean wanted that, badly. The thing of it was that he had given up on the simple dream a long time ago. After everything they had been through- the Apocalypse, Hell, Leviathans, The Trials, Angels trying to kill them, dying time and again only to come back and continue to gank the monsters they did on a regular basis; he didn't know how Sam could still hope to have a life like that eventually. Winchesters, hell hunters in general, just didn't get to have that apple pie life.
He had tried, God knows he had tried with Lisa and Ben. And for awhile he had had that life, but something had always felt off, like it was borrowed time. Then it all went straight to hell when Lisa got possessed and he almost lost them both. It was better they didn't remember him, at least that was what he told himself at night when all these thoughts were swirling in his head and he couldn't sleep.
He remembers his daughter Emma, as brief as her life was, because Sam had ended it. He knows deep down where it matters that it was necessary, but it doesn't make remembering her any easier. She had looked more like her momma, but Emma had had his chin and nose, his bearing. Intrinsically he had known she was his. He yearned for that feeling back. However, it would gut him as nothing else had if he were to lose a child again, better to be lonely and driven then have that dream taken away.
Sammy didn't know him completely, although it was close. Dean had made sure to hide that vulnerable dreamer side of himself because Sam had needed him to be strong for so many years. Still did truth be told, but now it was a different kind of strength. Cas needs him to be strong and Kevin too. He has a family, it might not be the one he used to dream of, but they are his family and he will do whatever is necessary to keep them all safe.
Dean can live with that he tells himself even as he slips into sleep, tear tracks starting to dry on his cheeks. He has to.
So this was just a little drabble that came to mind upon thinking of Dean and his daughter and how Dean might have wanted the life that Sam always dreamed of. Please let me know your thoughts if you feel so inclined. I looked it over, but it was not beta'd so any mistakes are solely mine, sorry.