The next afternoon in the bunker, Sam couldn't contain his curiosity as Castiel entered the room.
"How was your date, Castiel?" Sam interrogates, his eyes bright with anticipation, his focus shifting from the map table where he had been working on making connections on a job they're looking into.
Castiel paused, a hint of a smile playing on his lips, "it was fine," he replied, his voice carrying a sense of contentment. "It was..fun."
Sam practically beamed with excitement, "that's great Cas. What did you guys do?"
"We went to the pizza place, then walked to the motel," Castiel explained. "We kissed."
Sams eyebrows shot up in surprise. "You kissed Meg?"
Castiel simply nodded "yes."
"Huh," Sam hadn't expected things to progress that far, but he understood that they were willing to go to great lengths to get Dean to admit his feelings for Castiel. "How was it?"
Before Castiel could answer, Dean strolled into the room with an ancient, torn book in hand. "How was what?"
"I was asking about cas's date," Sam replied, his tone casual. "He was just about to tell me how the kiss was."
Dean rolled his eyes and threw the leather book down on the table, clearly uninterested in the conversation.
"It was good I think," Castiel responded to Sam's questions. "We have kissed before, but I don't really have a lot of other kisses to compare it to."
Sam, always the one for humor, took a step closer to Cas. "Do you mind? We can kiss if you want, see how that goes."
But before any moves could be made, Dean intervened, grabbing Castiels bicep and quickly ushering him toward his room, slamming the door shut behind them.
"Dean?" Castiel questioned, his confusion evident.
Inside the room, Dean paced back and forth, trying to find the right words. He needed to get this off his chest, consequences be damned. "Do you like Meg? Or hell, Sam for that matter?"
"They're my friends—" Castiel began, but Dean didn't let him finish.
"No," Dean shook his head, his frustration building. "Do you like them? As in want to be with them."
Castiel took a moment to process the intensity of Deans questioning. "No."
"Then why—why go out with Meg? Why kiss her? Why almost kiss my brother?" Dean's voice was filled with desperation.
Castiel sighed, attempting to get a read on Deans emotions. "Dean—"
"I like you," Dean blurted out abruptly, his words hanging heavily in the air. "I like you a lot more than just a best friend, Cas. Hell, I think I'm in love with you. I don't think I can see you with someone else."
"You love me?" Castiel asked, his eyes widening with realization.
"I think so," Dean admitted, his voice barely above a whisper.
A smile graced Castiels lips as he confessed, "I think I love you too."
Without further hesitation, Dean closed the distance between them, and their lips met in a passionate heated kiss. It was a long-awaited moment, a culmination of years of unspoken feelings and shared experiences. In that kiss, they found the courage to confront their emotions and embark on a new chapter in their relationship.
Eventually, Cas had to pull back for air and he asks, "are you sure you want to do this, Dean?"
"I've wanted this for years, Cas. Years. I'm sure."

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Operation make Dean jealous
FanfictionFive times Dean Winchester Is jealous and the one time he actually does something about it.