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The scenery outside the windows of the train blurred together, greens from the trees blending with the deep blues and purples illuminating the twilit sky, browns from the trees meeting the tans from the dirt road nearby. Without knowing how he got on the train, he knew his destination: St. Mary's Convent in Ilchester, Maryland - the place where everything started; when Sam killed Lilith there, with the final seal undone, Lucifer broke free. Destiny began turning her wheels, Sam would say "yes" to Lucifer, and Lucifer would be imprisoned once more thanks to the four keys.
But they wouldn't have known about the keys without the help of one Archangel, the one who Dean found himself missing more than he would find comfort with Lisa. The same Archangel sitting across from him right now on this train, despite Dean knowing for a fact that he was killed by Lucifer himself. This was in fact a dream, one he found himself in quite often lately. No matter how many times he rode in this train, though, Dean couldn't look Gabriel in his eyes. Gabriel hadn't wanted to face Lucifer; sure, it was the cowardly way out of this fight, but he hadn't wanted to take part. Yet Dean didn't listen, and now Gabriel is dead.
The guilt pooled in his stomach as he watched the skies darken; the pies in front of him grew cold, but he couldn't take a bite. Nausea overtook his senses as he looked from the window to each pie, knowing that Gabriel had an expectant smile on his face. Dean was the reason Dad wasn't there, the reason Gabe died, and the reason Sam wasn't there. The deeper he went into thought, that pit in his stomach, an insatiable hunger for love, family, and happiness, grew larger, no end in sight.
The train's horn broke Dean out of his thoughts and without thinking, he looked into Gabriel's eyes. Pure love, affection, and empathy shone brightly, and his smile spoke volumes. It was almost as if this look were saying that everything would be fine, he's okay, and Dean shouldn't feel bad at all. Except everything wasn't going to magically improve because Gabe isn't really here, and the look made Dean feel worse. Gabriel's lips began to move, but before Dean could comprehend what he was saying, the train entered a tunnel and all lights blinked out, the sound of the hard working engine echoing off of the walls grew quieter and quieter until everything was silent.
Dean slowly opened his eyes from the familiar dream feeling more empty than ever. No amount of crying would fix what had happened, and he knew his grief was getting stronger. The dreams he'd been having about his former lover felt real, too real. It was finally time to seek help; a psychiatrist could aid him in overcoming this grief. Maybe someday, he could remember Gabe without this pit eating away at him, but right now, Dean ached to forget.