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Dean looked at himself in his fifth glass of whisky, ignoring the rowdy bar around him. The air was smoky and classic rock blasted from old speakers in the back. Dean didn’t look away from the eyes staring back from the glass. They were red and hollow. They didn’t look like his.

Sam had offered to come with him that night but Dean had shaken his head no. Dean’s self-designed punishment was suffering without the comfort of brotherly company. Sam was worried about his older brother; he didn’t do much talking these days. He didn’t do much of anything.

Dean’s life had become a mind-numbing string of bars, shots, and chicks. Tonight was just like any other. Unaware of the gap teeth and faded tattoos that surrounded him, Dean was immersed in bittersweet memories that tormented him endlessly. He was with Y/n.
Their first date was in some small town diner, a relic of classic Americana. A buzz of excitement followed the couple to their booth and innocence danced in the night air. His hands were sweaty and her cheeks were pink. They both got the bacon cheeseburger with all the fixings and Dean grabbed the bill before Y/n got the chance. They were fresh faced then, oblivious to the path in front of them.

Dean’s face twitched into a painful smile. He was back in the Impala, glancing over at Y/n in the passenger seat. Open windows brought in summer air and Dean couldn’t suppress the soft smile that graced his face. Y/n’s painted toes were on his dashboard and her face was hidden behind a map. Sam had been kicked to the back; he complained for the whole trip. Dean remembered the first time Y/n’d slept in the front, the first time he had to drive one-handed because his fingers were interlocked with hers, and of course the first time Y/n drove Baby. Dean’s heart was in his throat as she turned the ignition and shifted into first but he couldn’t help notice how the sun played in her hair and how sweet her smile was.

A girl slid next to him, she smelled like cigarettes and acetone. She asked if he was here all by his lonesome and if he needed a little company. Dean ordered two more shots of whisky, neat, and stood. The girl took him by the collar of his worn leather jacket and led him onto the dance floor. If someone were to have asked Dean what the girl looked like, he would have been hard pressed to answer. In his mind, it was Y/n’s hand holding onto him, her eyes flirting with him. He was not in some bar; he was being pulled across the white sand beach he and Y/n had visited last summer. Y/n had worn pink flowers in her hair and there was a playfulness in her eyes that Dean knew well. Dean had held Y/n in his arms as they swayed in time to music that wasn’t playing. He spun her. She laughed.

The older brother blinked his tired eyes and pressed his lips to the stranger’s neck.

Then of course there was the day a storm picked up and Dean had to pull over as the roads started flooding. Y/n wiggled her way onto his lap and kiss him. He rubbed her hands together in the chilly air as the rain beat down on the roof. And with their breath fogging up the windows and hanging in the air, they promised each other they’d never leave; that this was forever and there would be no one else.

Dean pulled the stranger closer as she grinded up against him.

But then came the bad days and the fights and the tears. He’d shout, she’d yell, he’d swear, she’s cry. Dean would never forget the countless nights he spent on a cold motel floor outside the bathroom begging her to come out. He’d beg for forgiveness. Just baby open the door I didn’t mean it, baby please I can’t stand to hear you cry.

Fate turned on them with vicious teeth and as she walked out of his life, Dean saw his whole future go with her. Slow days in rocking chairs and greying hair vanished before his eyes. He stood in the doorway of some Nevada motel and watched her tires kick up dust. He punched a hole in the wall. He spent that night in the ER.

Dean’s life crumbled and it crumbled fast. He knew, but did not want to know, that no matter how many girls he was inside, no matter how many drinks he downed, he’d never numb the tear in his chest. The pain followed him, day in and day out, making him sick with grief. Y/n was the best thing to ever happen to him, his God give soul mate, his one relief in a world of anguish, and he had let her slip through his fingers. She would find someone else, someone better, and he would stay sinking into the past.