May 5, 1996

Castiel took shelter from the unseasonably warm sun in the shade of an oak tree and watched the river flow by. He glanced at the sky and frowned. It wasn't as if they kept to a strict schedule, but the Winchesters were usually here by now. Closing his eyes, he reached out, seeking the brothers' location. His frown deepened. They weren't together – Dean was quite near, but Sam was still in Sioux Falls.

A few minutes later, Castiel heard Dean making his way down the path to the water, so he stood and shook out his wings, yawning and stretching out the kinks after the long wait.

"Hey, Cas," Dean called as soon as he came into view through the trees.

"Hello, Dean," Castiel greeted him. "No Sam today?"

Dean lifted a shoulder in a lazy shrug. "Naw, me and Bobby got him an N64 for his birthday, so he and his friend Barry have been playing Mario for the last two days straight."

Castiel didn't understand all of that, but gathered he was referring to a game. "I guess he liked his gift, then."

"You could say that." Dean picked up a couple of rocks before flopping down in his usual spot on the riverbank and leaning back against the fallen log there.

Preferring to keep his wings free, Castiel sat atop the log instead. "Have you been well?"

Idly tossing his rocks into the water, Dean hesitated before answering, "I guess."

"Are you trying to convince me or yourself?"

Dean paused mid-throw, his hand dropping back down to his lap.

"Did something happen?" Castiel pressed.

Expression darkening, Dean seemed to shrink in on himself. He shrugged limply.

"Dean." Castiel waited until Dean looked up to meet his eyes. "What happened?"

"Look, it's not that big a deal, okay? It's nothing." Dean couldn't hold his gaze very long, and Castiel could see the shine of unshed tears in his eyes before he turned away. He threw another rock, much harder this time. "It's fine."

Castiel scooted down from his perch on the log to sit beside Dean on the ground. He put a hand over Dean's wrist before he could fling another stone and felt him relax minutely at the touch. "It's clearly not fine."

Dean kept his gaze out over the water. A tiny tremble began in his lower lip until he bit down on it. His face screwed up as he tried to keep a rein on his emotions, perhaps forgetting that Castiel felt everything he did. He sighed in defeat, his shoulders slumping even more. "Amanda Heckerling broke up with me."

The last few times Dean and Sam had met up with Castiel here by the river, Dean had spoken of this girl. He'd seemed so light and happy these past few weeks, but now it seemed the same girl was the cause of his current pain.

"Why?"

"She said she didn't think we were a 'good fit'." Dean picked at the ground-in grease that always lingered in the creases of his knuckles and beds of his nails no matter how much he scrubbed. "We were gonna go to prom, but I told her I couldn't do a lot of the stuff other people do, like get a limo and fancy food. My Baby's better than a limo anyway, and food's food, right? We could still go and dance and see people and have fun. But that wasn't good enough, I guess. I'm not good enough."

Dean's cheeks had turned a blotchy red. "I really liked her, Cas. And I know I'm nothing special, but I thought she liked me, too."

"Don't say that," Castiel reprimanded sharply. "Of course you're special."

"Yeah, sure," Dean muttered.

"Dean..."

"But, Cas, she's right," Dean insisted miserably. "I'll never be like her. She's smart and classy and lives in a big, fancy house, and her parents are both doctors, for crying out loud. I'll be lucky to graduate high school."

"Dean, stop it. You've taken care of yourself and Sam almost your whole lives, despite being a child yourself. You're strong. You're smart and capable. You're a wonderful person, Dean – kind and thoughtful and giving. And if this girl cannot see you for who you are, then she's the one who's inferior."

Dean flushed again under the fierce defense of his character. "Okay, okay. Jeez."

Castiel smoothed his feathers, which had ruffled up in his agitation. "I apologize, Dean," he said softly. "I didn't mean to make you uncomfortable. And I'm sorry this girl has hurt you."

After an awkward silence, Castiel added, "How are things other than that?"

"Fine, I guess," Dean said with a sigh. "They're gonna keep me on at the garage full time over the summer. If I keep working for Bobby on the weekends, too, I'll be able to save most of the money for Sammy's college fund. He wants to be a lawyer. Can you believe that? Sure, he's plenty smart – the little nerd's a total genius – but I don't think he's enough of an asshole to be a real lawyer."

Dean smiled tightly at his own joke, but Castiel just felt sad. Money was always at the front of Dean's mind. He hated being a financial burden on Bobby, and had finally convinced the man to let him work at the scrap yard on the weekends as a small contribution to supporting him and Sam. Castiel had never met him, of course, but he had the distinct impression that Bobby only agreed to it to make Dean feel better, not because he needed the help.

"I'm sure Sam will be successful no matter what he chooses to do," Castiel commented.

"Yeah."

Dean fell quiet again, concentrating on throwing more rocks, aiming them at a mossy boulder that peeked out of the water a ways out from the bank. Eventually he ran out of rocks, so he started scratching in the dirt with a stick instead.

"Hey, Cas?" he ventured.

"Yes, Dean?"

Adding fiddly details to his dirt drawings, Dean kept his head down. "Do you really think all those things you said? About me?"

The timid question pulled at Castiel's heart. It distressed him to know how little Dean thought of himself. "Yes. All those things and more."

Dean didn't look up or respond, but the tension in his shoulders eased. He scribbled his fingers through the dirt, erasing what he'd drawn, and began picking at the loose bark on his drawing stick instead.

Castiel watched Dean, knowing it would take him some time to process what he'd said. Castiel would never say so aloud, but he was suddenly very glad Sam hadn't come today. Usually he loved spending time with Sam, too, but he was quite sure that Dean would never have spoken of any of this had his brother been present.

At last, Dean threw the stripped stick into the water and watched it float sluggishly in the eddies by the bank before catching in the greater current. "Hey, Cas? You wanna swim?"

Castiel smiled. "Yes, that sounds good."