You weren't like Rory at all. Despite being twins, you could not have been more separate people. Rory was dedicated to academics while you were always out doing something, meeting someone, partying somewhere. It was so refreshing to Dean. He adored you. Every time Rory would hurt his feelings his first call was to you, telling you everything while you soothe him and make him feel better. He knew you just wanted your sister's relationship with him to go smoothly…but he was starting to want to call you just…to call you. He saw you plenty; you went to Stars Hollow High, cheered on the cheer team, volunteered at the theater productions. But he wanted to see you outside of school. Rory was messing around with Jess, and Dean was heartbroken despite his dwindling feelings for her. He'd waited for Rory to call him all damn night since Lorelai had advised him to just give her space and she would come to him. But she didn't. It was dark and Dean was sitting on your doorstep when you and your mom get home from taking Rory to Lane's house.

"She likes Jess, doesn't she?"

Dean's voice breaks as he looks up, dark hair falling across his forehead. Oh, your heart just broke to see that look in his eyes. He gets up, starting to walk away, but you follow.

"Dean…Dean, I really don't know."

Your arm wraps around his side and he sighs, slowing his pace so you could walk together.

"I just don't get it. I…I try so hard to be there for her and…and I know I'm not as smart as she is but…I didn't think she'd just dump me for Jess."

Dean whispers, his voice quiet and hurt.