Castiel went to drop Charlene off at her apartment after they drove around for an hour "practicing". She walked around to the driver's side of the car on her long legs and then knelt down to Castiel. She leaned in and gave him a small peck on the cheek.
"For good luck," she said with a sweet smile. "Not that you'll need it. You've got this, Castiel. He's going to love it."
Castiel smiled weakly, his body humming with nervous energy. "How do you know for sure?"
"You take care of him, look out for him. You're the highway, Castiel. The sky. You're his angel, I know it, and he loves you for it." With that, she poked him gently on the nose with her index finger with a "boop", stood up, and gracefully walked toward the door of her building. Castiel was taken aback. Could she know? How?
Charlene looked over her shoulder and called out, "and Castiel? When this is all said and done, you better come find me and tell me all about it."
She began unlocking the door as Castiel called out, "but what do I do if he-"
Charlene turned. "Boop!" she called back with a grin, poking the air with her index finger, and with that she disappeared into the building.
Castiel sat in the car as it idled, summoning the courage required for his new mission. He could easily transport the car back to the bunker without driving it at all, but he decided he needed a bit more practice before the final attempt. He put the car in reverse and as he pulled away he heard Charlene shout his name. He looked up and saw her head poking out of the second floor window, waving and grinning.
"Castiel, don't forget! 'Charlene' is an excellent baby name!"
Upon arriving at the bunker, he parked the Impala around the side. He sensed Dean was peacefully asleep, a mercy in and of itself. When he teleported inside and came face to face with Sam, he was initially worried about incurring some sort of vengeful, brotherly wrath. The ebullient greeting with which he was met significantly bolstered his courage. Charlene was right, I do in fact 'have this'.
"Cas," probed Sam, "why do you want to know about Lloyd Dobler?"