Dear Cas

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*FEELS*

*Twist and Shout Spoilers and references. Read at your own pain*

Leslie Rosen has known Dean Winchester as long as she can remember.

Dean Winchester, the old man who lives alone in the sad house at the end of the street.

Dean Winchester, who has a veteran sticker next to a peace sign on his car.

Dean Winchester, the old man who used to babysit her. The man who she kept visiting because he always looked so sad and she thought he could use the company.

"You remind me of my niece," He told her one day. "Sammy's little girl. She has blonde hair like yours, just like her mother's too."

Dean is 90 now. His brother and sister in law died a few years back, but Dean still liked talking about them. 

The outside of Dean Winchester's house is bare. Unwelcoming, and just as sad as the old man's eyes. But inside is different. Inside his house there are pictures. Dozens of pictures of him, racing on motorcycles, hanging out with his brother, his friends and family.

And one day, Leslie spotted an old, faded Polaroid picture of a young man with bright eyes and dark hair. 

"Who's that?" She asked, at only eight years old. Dean always had great stories behind the pictures, funny and sad stories of his friends and the people he loved.

But this picture was different. Dean had stared at his, and his eyes had gone glassy.

"You're too young to hear about him," He had whispered. He had asked her to leave shortly after, and Leslie got the feeling it was because he cried after she left.

Every year she would ask, and every year she got the same answer.

"You're too young to hear about him."

And then one day, the answer changed.

When Leslie was sixteen, same-sex marriage became legal in all fifty states of the U.S. It had been a proud day, and Leslie's girlfriend had given her a rainbow flag pin in honor of it.

Leslie thought nothing of the pin as she went to visit Dean Winchester, only to see him gazing at his TV, the news clicked on where they were talking about how the marriages were legal everywhere in the U.S. now.

"All fifty states now," Dean whispered.

"Yeah, isn't it great?" Leslie questioned. She hoped Dean wasn't one of those old folks who was still bias against members of the LGBTQ community. Dean had been her best friend for years; she couldn't bear the thought of him disliking her. Instead, Dean had looked up and studied her with an unreadable expression.

"That's a nice pin," He commented finally. "What does it mean?"

"It's the gay pride flag," Leslie offered. Dean nearly winced.

"Pride?" He echoed.

"Yeah, a pride flag. My girlfriend gave it to me." Dean had smiled softly.

"You have a girlfriend?" He asked deviously. Leslie grinned.

"Yeah, her name is Charlie. We've been dating for a few years now."

"Do you love her?" Leslie nodded frantically.

"Definitely. She's amazing." 

Dean stood and walked over to his pictures, looking through them before finally picking up the one of the mystery man.

"Do you still want to know who he is?" He asked.

"Of course," Leslie declared. Dean's hands were shaking slightly as he handed her the picture.

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