"Well do you wanna grab the pizza with me?" Dean asked the younger Gilmore sister, knowing that's what Rory would want him to do. "We could walk back to the house together."

Cassie opened her mouth to say hell no but just as she was about to do it Rory's puppy dog eyes appeared in her mind. She could practically hear her sister begging her to go with Dean. "Sure."

"Cool," Dean held out his arm, saying he was following her so Cassie started walking. They were quiet for the most part, but they both knew Rory would want them to talk. "This is kind of awkward, isn't it."

"Yes it is," Cassie nodded.

"You don't like me?" Dean asked her, looking down at her.

Cassie sighed, looking up at him. "I don't not like you," She replied, but apparently that wasn't the answer Dean wanted to hear. "You're Rory's boyfriend, and she obviously likes you, my mom likes you-"

"But you don't?"

"I'd like to," Cassie admitted. "It'd be a lot easier for all of us if I liked you."

"Yeah, it would," Dean laughed awkwardly. He looked over at Cassie who now wore a guilty expression, she knew it was her fault she and Dean weren't friends. He had tried to talk to her plenty of times, but every time he did it was like she took a vow of silence. "Well usually friends have something in common."

"Something in common?" Cassie questioned, like the concept was completely new to her.

"Yeah," Dean nodded. "Rory said you liked baseball."

"Like is a bit of an understatement," Cassie laughed.

"I like baseball," Dean informed her and Cassie looked up at him with a questioning look. "I'm more of a cubs fan myself."

"Of course you are Chicago," Cassie said, shaking her head at her. "You should go to a real game. In New York."

"Do you go to games a lot?" Dean asked her.

"Mom and Rory never liked going, but my dad took me... once," Cassie answered, the smile on her face turning into a frown. "I'd like to go again, though." She said, going back into a more cheerful mood.

"You should come to the games Luke and I play," Dean told her. "I think you'd like it."

"Maybe I will," Cassie said.

Turns out being friends with Dean wasn't as hard as Cassie thought it would be. They picked up the pizza and Cassie teased him about ordering a salad. Which naturally led them to conversation of lettuce: friend or deadly poison? But they were actually getting along, so when they finally walked into the Gilmore house they were both laughing.

"Hello?" Dean called out when he opened the door.

"Do you come bearing pizza?" Lorelai yelled from the living room.

"I'm not an idiot." Dean told her as he walked into the house, with Cassie following behind him.

"Then get in here."

"Hey," Rory smiled at her boyfriend and her sister.

"Hey."

"I'm putting the ice cream in the freezer," Cassie announced then quickly left the room.

"Sit - you're missing it." Lorelai said when Cassie reentered the room.

"What are we watching?" Dean asked.

"The incomparable Donna Reed Show," Lorelai told him.

Cassie sat down on the floor on the other side of Lorelai. Rory looked down as Dean set the pizza down, her head tilting in confusion when she noticed a brown bag on top of the pizza box. "What's in there?

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