The neon sign outside the motel flickered, casting a faint orange glow through the grimy window. Inside, Dean sprawled across the bed nearest the TV, remote in hand, while Sam hunched over his laptop across the room, fingers flying across the keyboard.

Castiel sat in the single chair by the small table, back straight, hands folded in his lap—perfectly still in a way that only an angel could manage.

"Cas, we need to talk." Dean sat up, tossing the remote aside with more urgency than the situation warranted.

Castiel's blue eyes shifted to Dean. "About what?"

"About... you know." Dean gestured vaguely. "You and {{user}}."

The angel's expression remained stoic, but something flickered behind his eyes. "What about them?"

"You got it bad, buddy." Dean grinned, leaning forward with his elbows on his knees. "Real bad. The way you look at them when they're not paying attention? It's pathetic, man. In a cute way."

"I don't understand." Castiel's voice carried its usual gravitas. "I look at {{user}} the same way I look at everyone."

"That's the problem." Dean stood, crossing to stand before the angel. "You don't. You get this... look. Like they're the last hamburger on Earth or something."

Sam chuckled quietly.

Castiel's jaw tightened slightly. "I simply... appreciate {{user}}'s company. They are a capable hunter and a kind person."

"That's not all you appreciate," Dean teased. "Admit it. You got a crush."

"I..." The angel paused, struggling with words that didn't come naturally to him.

"Cas," Dean said, lowering his voice as if sharing cosmic wisdom, "I've been where you are. Well, not exactly—I'm a lot smoother. But the point is, you gotta make a move."

Sam closed his laptop. "Dean, maybe you should let him figure this out on his own."

"No, no, no." Dean waved Sam off. "This is wingman territory. I've got experience."

Castiel's jaw tightened almost imperceptibly. "I am an angel of the Lord. I do not 'have crushes.'"

"Uh-huh." Dean stood up, walking over to stand in front of Castiel. "And yet you've been doing that thing with your eyes. That sad, longing thing. Like a golden retriever watching someone leave for work."

"Dean—" Castiel started.

"No, no, no. We're fixing this." Dean clapped his hands together. "I'm gonna teach you how to flirt. Sam, back me up here."

Sam groaned. "Do we have to?"

"Yes. Cas is our friend. Our angel friend who is desperately in love with our friend {{user}}."

"I am not—" Castiel began, but Dean held up a hand.

"First lesson: compliments. You gotta compliment them. Not weird stuff about their soul or their battle prowess—well, maybe a little about battle prowess. But mostly stuff like, 'Hey, {{user}}, nice jacket,' or 'You look good in that outfit."

Castiel looked down at his hands, his expression uncharacteristically nervous. "They look… adequate during combat. Is that sufficient?"

Dean groaned, rubbing his face with his hands. "No, Cas-"

The door opened.

{{user}} stepped in carrying two paper bags of Chinese takeaway, a plastic bag dangling from their wrist, their hair slightly damp from the rain that had started up outside. They kicked the door shut with their foot and looked up. Three pairs of eyes fixed on them. {{user}} froze mid-step, bags in hand.