Sam hated the way his life had been developing under his father's guidance, as the life of a Hunter was never what he wanted for himself. John had raised his children to be soldiers, unsung heroes who will be cursed to protect humanity and sacrifice all they’ve got just for a glimpse of freedom from what hides in the shadows; he wasn't a father in anything but name, more akin to a sergeant. And although Dean grew up with the knowledge of the supernatural, he did his best to ensure his baby siblings’ blissful ignorance for as long as he could—until you and Sam found your father's journal at least.

After that discovery, everything slowly started going downhill: Dean was introduced to the ways of the Hunt, while the two younger siblings were forced to keep each other company in lonely motels, trying to focus on what little studies you two could do given the lack of books or computers at your disposal. This process kept repeating for years, until Sam was deemed old enough to also start training and killing demons, which in turn left you, the youngest Winchester, all by yourself. It killed Sam to think about that, knowing how scary it must be to wait for what's left of your family to return and never knowing if you're actually safe in those crappy motel rooms.

Nevertheless, both of your brothers still tried their best to include you, Sam being the one who stepped up the most for you. Not only did he get mad at his father for forcing the Hunting life upon him, but he also kept exploding whenever John would mention dragging you into it when you've clearly expressed that you wanted nothing to do with it. Neither you nor Sam wanted to deal with all of the supernatural bullsh*t, you both just wanted to become normal students and lead very mundane and normal lives, but that's something your father and your oldest brother, Dean, didn't much agree with.

However, Sam had enough. An awful fight broke out between him and John, which led to Sam ultimately leaving the family to become a law student at Stanford. For once he put himself first before his family, chasing his dreams... but leaving you behind would perhaps be his biggest regret for the rest of his life. He cut contact with everyone, you included, and in hindsight maybe he could've brought you along, could've taken care of you—but it's a little too late for that, isn't it?

Sam could see it in your eyes the day you two met again after 4 years: the look of a Hunter, and a tired one at that. You clearly weren't as good at hiding your inner discomfort as Dean, and Sam wasn't sure how to approach you anymore. You went from a somewhat jolly 15 year old that followed him around like a puppy, to a quiet 19 year old that barely meets his gaze. He truly misses the ray of sunshine you used to be, but he can’t turn back time, so Sam can only hope that you'll forgive him for abandoning you—because that's what he did. He ran away and left his poor little sibling behind, the one who always counted on him to protect them... He royally messed up, but he's determined to slowly rebuild the sibling bond that he misses so much, no matter how long it takes.

"Hey nugget, guess what?" Sam smiles softly while slowly rattling a paperbag, "Gotcha donuts and some tea. I asked Dean in advance to be sure that I'd get you a flavour you like, no worries." He says so while putting down the items in front of you, taking a seat opposite to yours to try and do some small talk. "So... what have you been reading lately? I noticed that you still bring books to read during long car rides and—Oh! Have you learned how to drive yet? I could teach you if you want to, Dean would be too busy telling you not to scratch ‘his Baby’ to give any actual directions." He tries a little joke at the end of the sentence, hoping to at least make you crack a smile.