As soon as the door closes behind Cas, Charlie's teasing ends as well. The silence that falls is tense, and for the life of him, Dean can't figure out why.
"So," Charlie says tentatively, obviously picking her words with care, "how're you doing with all this, Dean?"
He hates it, but since there's really not a good reason for that, Dean plays dumb. "What're you talking about, Charlie?"
He regrets the decision as soon as the pillow comes over the edge of the bed and slaps him in the face. "Don't play dumb with me, Winchester!" Charlie admonishes.
Dean scrambles up and throws the pillow in his lap. "What the hell!" He sees Charlie brandishing the pillow from Cas's pallet and holds his hands up in surrender. "Uncle! Uncle, okay!?"
Charlie watches him speculatively, slowly lowering the pillow. They have a brief staring match before Dean sighs in defeat, rubbing at his face tiredly.
"I don't like it, okay? I don't like him," Dean growls. "Cas deserves better."
Charlie sighs. "Dean, you don't even know Balthazar."
"Neither do you!" he spits back.
"True, but at least I'm giving him a chance."
"Well that's your choice. I don't see why I should have to do the same," he grumbles petulantly.
"Because Cas is your friend, and he's happy. He at least deserves you not standing in the way of that."
"'M not standing in the way," Dean mumbles, and even he knows just how childish he sounds.
"Dean, you know what's right and what's wrong here, so it's up to you whether you're going to be an ass about it or not," Charlie says, and Dean can hear the disappointment in her tone. "Now I'm going to sleep. You do what you want."
"'Course I can. It's my damn house," Dean grumbles in one last ditch attempt to... To what? Prove he's right, even when he knows he's wrong?
As Charlie's breathing evens out, guilt claws up Dean's insides. Is he still being a shitty friend? The thought makes him want to hit something! It seems like no matter what he does, he keeps hurting Cas. Well, not anymore! Dean vows to himself that he's going to do everything in his power to be the supportive best friend Cas deserves. Besides, it's their last year together before they're off to college. Does Dean really want to waste it in a string of pretty fights? The answer is of course not, yet Dean still can't get over this feeling. He's about resolved to go and get Cas so they can talk this out when the door opens again, and Cas silently makes his way across the room to his blanket pile. Something twists in Dean's gut, making him feel sick. Is Cas really happy? Does he really like that sleaze bag?
He screws up his courage and whispers into the darkness, "Charlie fell asleep. Was about to come check on you."
"Sorry," Cas replies quietly, and shit! Cas doesn't need to apologize.
"S'cool." Dean Winchester, ladies and gentleman, douchebag extraordinaire, making best friends feel guilty for their relationships since 2009!
Dean screws his eyes shut, wishing desperately he could fall asleep, if only the guilt would leave him alone long enough. Even if he doesn't think he wants to know the answer, doesn't want Charlie to have proved him wrong, he has to know. For Cas's sake.
He summons up the courage to ask, "You really like him, huh?"
He can hear the damn smile when Castiel responds, "I think I really do."
Dean steadfastly ignores how his stomach sinks with that admission and thinks that decides it. Dean's just going to have to ignore his hangups about Balthazar and support Cas. After all, that's what best friends do.
The next morning, it's like nothing ever happened. They're all back to joking and hanging out like they always have, not an issue between them. They get up and have a stupidly-early-for-a-Saturday breakfast before Charlie heads off down the street to her house and Dean drives Cas home.
When the Impala pulls up in front of Cas's house, Dean slides her into park and turns to look Castiel in the face.
"Cas, I hope you have fun today," he says with as much sincerity as he can muster, which is a surprisingly large amount. Even if he's not fond of the company Cas will be keeping, Dean really does want him to have a good time.
Cas stares at him in confusion for a moment, brow pinched together and head tilted to the side. Finally, he offers a small smile and says, "Thank you, Dean. I hope so as well. And same to you and the others. Perhaps next time Balthazar and I will be able to join you all."
Dean ignores the way his stomach churns acidicly at the thought that there will be a next date for Cas and Balthazar and, instead, says, "If you need anything, don't hesitate to call me, okay? I'll come and get you as fast as I can."
An odd sort of amusement flickers across Castiel's face, and he laughs softly. "Okay, Dean, I will. Thank you."
Dean offers a strained smile in return. "Any time, Cas."
Dean watches as Cas slides out of the car and heads to the door, driving off only once Cas is inside. He pushes aside the feeling of being sick, wondering if it was something he ate. The only way he avoids hoping the sausage this morning was bad enough to ruin Cas's date is by reminding himself that he has his own in a few hours.
The whole way through the double date, Dean is habitually checking his phone, and every time he does, there are no missed calls or messages. He tries to tell himself that he's glad and that it's a good thing. After all, that means they're having a good time right? Dean's happy for them. Now, if only that didn't sound so sarcastic every time he tells himself that.
On the other hand, no contact could mean that something has happened, that Balthazar has kidnapped or hurt Cas in someway. When these thoughts cross his mind, he can't help excusing himself to run to the bathroom and call Cas. Every time, he just ends up staring at his phone long enough to talk himself out of it and returns to the group feeling like an idiot. He said he was going to give the guy a chance, didn't he? Cas deserves that much from Dean.
The whole situation gets so bad that at one point during dinner, Charlie kicks him in the shin under the table. It hurts like a bitch and is enough to make Dean put his phone away for the remainder of the night.
It isn't until Dean and Anna are alone, Charlie and Dorothy having run off to be left to their own devices, that Anna brings it up. Honestly, Dean's kind of shocked it took this long. He's been a horrible date, and he knows it.
"Pull over," she instructs. He winces, but does as she says. He puts the car in park and turns to face her. She's studying him with concern. "What's up with you today?"
He scratches the back of his neck, a nervous tick, and as soon as he does it, he knows he's screwed. Still, he plows on, not quite making eye contact. "It's nothing, Anna."
"Bull!" she proclaims and exits the car, making a show of slamming the door. Dean would yell at her for it if she wasn't justified.
He scrambles out of the car and shouts, "Anna, wait!"
She doesn't stop walking, doesn't even look at him as she calls back, "Screw you, Dean Winchester!"
"Damn it!" Dean quickly leans into the car to turn the key and pull it out. "Anna, come on!"
He catches up to her easily and places a hand on her shoulder. When she turns around and glares at him like she wants to set him on fire, he immediately pulls back.
"No! I won't wait!"
"What are you going to do!? Walk half way across town!?" he yells back.
"Maybe I will!" She turns back around and starts walking again.
"What the hell did I do!?"
She spins around and stalks towards him, jabbing a finger into his chest hard enough to bruise. "I knew you had a reputation! I knew what everyone said, but Castiel assured me you were a good guy! Joke's on me, I guess!" Angry tears fill her eyes and spill over in ugly rivulets.
Dean holds his hands up in a placating manner. "Whoa, whoa, whoa! What are you talking about!?"
"Your phone, Dean! Just who were you talking to all day, huh!? Who is she!?"
Dean tries so hard not laugh, knowing it won't help his case. He fails all the same.
"Screw you, Dean!" Anna yells in the face of his amusement.
He wraps his arms around her. "Wait, Baby, wait. Hang on."
"Let go of me!" she cries, struggling against his hold on her.
He steps back, laughter subsiding. "Anna, I was trying to see if Cas was calling."
Anna narrows her eyes suspiciously. "You really expect for me to believe that?"
"You can ask him yourself," Dean promises with a comforting smile. "I was worried about him going that date with Balthajerk and told him to call me if he needed anything."
Anna's aggravation melts away into disbelief as she blinks at him. "Wait... you're serious?"
Dean's smile turns sheepish. "Yeah. Guess I'm just being kind of over-protective, huh?"
Anna cracks a smile, and while it's small, it's a start. "Well, we always knew that."
Dean wraps her up in another hug, and this time she leans into it instead of fighting it. "We good?" he asks.
She nods against his chest. "Yeah, we're good. Sorry for acting like such an idiot."
Dean pulls back enough to look her in the eyes. "Hey, no, don't apologize. I was acting fishy, I get that. But I hope you know I would never cheat on you. I really, really like you, Anna."
Anna's smile is shaky, at best, but Dean'll take it. As she playfully cuffs him on the shoulder, she says, "I guess I really, really kind of like you, too."
Dean kisses her softly before pulling back with a dopey grin and saying, "Good. Now let's get back to the car, okay?" When Anna nods her agreement, Dean slips his fingers through hers and leads her back.
Once they're all settled, Anna places a reassuring hand on his knee and says, "Hey, you know Balthazar is harmless, right? He's a good guy. Castiel will be okay."
Dean rolls his eyes. "That's what everyone keeps telling me."
He can't help thinking, But if that's true, why do I have such a bad feeling about this?