At Stanford, Sam dreams about a lot of things. He dreams about a future with white picket fences and neighbours, and a life where death is not an everyday thing. He dreams about earning money and providing for a family, about sleeping at night without a knife under his pillow. He dreams about having friends who aren't related to him and who haven't ever used a shotgun. He dreams about apple pie and a wife baking it.
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The first year at Stanford, Sam thinks that maybe part of growing up is realising that not all dreams can come true. He doesn't make any real friends the first year, because he can't tell them about his family or his childhood or his past or anything about his life, really. He tries to lie without remembering that Dean was always better at it and finds that it is easier to be silent and go unnoticed. After all, hasn't he spent a lifetime learning to be what the situation requires? The dreams will come later.
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He waits a month before calling Dean, because the hurt of how he left is a bitter hurt that holds the residual pain of an entire childhood, and it isn't easy to forget. But the bond of an entire childhood isn't easy to forget either, so after a month of struggling and remembering and forgetting all at once, he calls Dean. The first phone number is disconnected, so he tries the second but it's disconnected too and after that he loses his nerve. What if Dean doesn't pick up? He thinks maybe the hurt of that would be worse than the hurt of not knowing; so he doesn't call again.
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At the end of the first lonely year, he finds that he is faced with a whole empty summer and nowhere to go. He thumbs through his phone and discovers that all of the names are names from the world he's left behind, so he looks up a homeless shelter a couple states away and stays there for the summer, working at an actual real job every day. Some days he thinks about the jokes Dean would make regarding him holding a job, and some days he remembers that even though his father is an ignorant stubborn fool, at least with him Sam was never homeless. But most days he just works.
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One day after he has come back to school, he is reading a newspaper and he finds a story that clearly references a vampire. It's only about an hour away from him, and he sits silently staring at the newspaper until the sun starts to come up for the new morning. Then he opens his phone and scrolls through all the names of men who would wonder why he couldn't take care of it himself and he thinks about how his father would never leave a vampire out there without doing something and he flips his phone closed and goes to sleep. He wakes up a couple of hours later for classes and finds dried tear streaks on his cheeks - but then, his eyes always water more when he's tired.
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He meets Jessica during his second year, and she loves him even though he can't tell her who he really is. He thinks maybe he's getting better at lying, because she doesn't even seem to know that he is holding back. He ponders once, how proud Dean would be at his success in falsehoods; but then he remembers that he's a different person now and probably Dean is too and anyway, he doesn't care anymore what Dean would say.
He goes home with Jess for his second summer and thinks that maybe growing up isn't a releasing of all dreams. After all, he's halfway to the life he's always hoped for and it's looking more and more like this life could actually be something permanent. Maybe this time it will work out, and he won't have to leave it all behind for a new start. He's done that before, and he knows that new starts are not always beautiful things like people think.
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Jess asks him, during his third year of college, about his family, and he thinks that maybe the time has finally come for the truth. But she looks at him with such complete trust and innocence that he can't do it. He blinks and remembers how he cried when Dean finally told him who their dad really was and even though he's trying not to, he remembers how Dean comforted him that day too. So he swallows hard and tells her that he has a brother and a father, but they're not really close. A thousand moments flash through his head in that instant, of Dean bloody and needy and crying and comforting and protecting and soothing and teaching; and he remembers how they used to be able to talk without talking and how even now he could list all of Dean's favourite movies and meals and cars without thinking.
Jess asks softly what his brother's name is, and he says "Dean. His name is Dean" and grimaces at the untruth of it all. She thinks he's grimacing for another reason though, so they go to bed together and she helps him forget it all.
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Then one day, Dean shows up. He breaks in and Sam isn't surprised even though he is, and his heart stutters loudly with half-forgotten memories even as his mind drags up the old anger. His eyes would fill, he thinks, if he wasn't still so mad. But he is a man now, so he controls all of his emotions and he is calm and rational all the way until Dean drops the act for a split second and says "but I don't want to". After that, Sam finds himself packing and trying to explain to Jess and getting in the car that has always been home and driving away from what has always been hope. He wonders for a panicked moment if this is the end of his white-picket future, but he has always been good at dreaming so he chooses to believe he will come back. This trip with Dean is just a one-time thing, a repayment of all the things Dean has done for him.
So the whole trip is heartbreaking, because it dredges up old memories of the life he's been trying so hard to forget. He remembers how much he loves being with Dean and how annoying brothers can be and what it feels like to be completely honest with someone and why he left. He remembers all of it and he thinks he can feel his apple pie dreams shattering around him but he refuses to accept it. So it's ironic, that the first diner they stop at is advertising apple pie but they're all out. Dean complains loudly about that, and Sam wonders if there is a reason his brother has always loved apple pie. Maybe it stands for something more to him too. Or maybe not. Dean is, after all, a hunter through and through.
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At Stanford, Sam dreams about a lot of things. He dreams about his memories of Dean and he dreams about his childhood traumas and for the first whole week he dreams over and over again about Dean coming to Stanford. He dreams his life over again, reliving his every hunt and his every mistake and every word he's said that he wishes he could take back. He dreams about going home. But the only dream from Stanford that really matters is the one where Jess burns on the ceiling with her blood dripping gently onto his forehead. See, he didn't know it until later - but the end of his white-picket future happened before Dean ever showed up.
And much later, mature and hardened, he thinks that maybe all of Stanford was really just an illusion, and maybe losing your dreams really is a part of growing up; at least, growing up as a Winchester. Maybe this was always going to be his future - his only future. He is, after all, a Winchester through and through.