After Charlene's shift had ended the two of them stayed at the table and she peppered Castiel with questions about Dean "for research".
"First of all, what does Dean hate?" she asked, eyes narrowed.
"I know that he did not enjoy the time he spent in Hell," Castiel quickly replied. "Luckily, I was able pull him out."
"So you helped him through some tough times then, eh?"
"To put it mildly."
"What else? What else rubs him the wrong way?"
"He has a strong aversion to the the teddy bear from those fabric softener commercials," he said, deadpan.
Charlene shuddered. "Who doesn't? Okay, so… what does Dean fear most?"
Castiel's eyes drifted upwards in thought. "He is quite terrified of flying. Phobic, even."
"So no romantic trips to Puerto Vallarta in your future, huh?"
"Not on a plane, no."
Charlene shifted in her seat. "Now, Castiel, tell me: What does he love? What brings him pleasure?" Charlene smiled, blue eyes sparkling. She really was enjoying this, helping Castiel. She could tell he was so hurt, lonely, and scared. She barely knew the guy, but she ached on his behalf.
"Dean values family above all else," Castiel said automatically.
"So he's loyal, then?"
"To a fault."
"Okay, but that's a value. What does he enjoy? What makes him smile?"
Castiel thought for a moment. "Dean loves his car. It was left to him by his father." He paused. "Dean is very fond of classic rock music. He listens to it every day." He paused again, thinking. "He also has a very strong affinity for pie." Castiel let slide a small smile as he remembered their passionate embrace in Dean's dream, guitars thrumming and drums beating, his light filling the room as they pressed up against one another-
"Castiel?" Charlene waved her hand in front of the face of the angel whose attention had drifted far, far away. Castiel snapped back to attention.
"I'm sorry," murmured Castiel. "I was just thinking about-"
"Pie?" Charlene could not suppress the huge grin spreading across her face.
Castiel cleared his throat, a crimson tell burning across his cheeks. Charlene reached out and took his hand in his, and looked him dead in the eye. "Don't sweat it, Castiel. Everyone loves pie."
Castiel started to pace nervously. He stood behind Charlene as she leaned into the front seat of the Impala, rooting through Dean's cassette tapes. The sun was beginning to set, and the only thing Charlene had said to him as she led him out of the diner by the hand was, "Castiel, we're going to Lloyd Dobler the shit out of you."
"Nope, nope. What about this one-nope. Nope, no...nope," she said, picking up each tape, examining it, and tossing it onto the passenger seat. She leaned back and stuck her head out the door. "Your boy sure does love him some Blue Oyster Cult," she said with a smirk. "And Kansas! Adorable!" With that, she turned around and headed back into the fray.
"Charlene," he said, husky voice cracking with insecurity, "I am not exactly sure of your intentions."
"We have to find the appropriate song, Castiel," she announced from inside the car. "A song that says something about you. And him. And you and him. A song you can give him that will say all the things you need to say because it's-ah! Yes!" She leaned back out of the car, cassette held triumphantly overhead. "Because in situations like this, sometimes your own words fail."
She stood up and took Castiel's hand, and put the cassette in his palm with purpose. Castiel held it up and looked at it curiously.
"Audioslave? That does not sound uplifting," said Castiel with a grimace.
"It's not meant to be uplifting! It's meant to be passionate. You are hurt, Castiel. You need to define yourself outside of the context of your relationship with Dean. Sounds like he needs to do the same. Then you build a new relationship around that. Be the man you want Dean to love, not to settle for." She clasped Castiel's hand between her own and squeezed. "You are the highway, Castiel. Now come inside and help me carry some things. Then we'll drive around and practice."
"Practice?" Castiel's hoarse voice cracked.
"Castiel, one does not simply walk into Mordor."
"I do not think I understand that reference."