Dean X-Reader - The Ultimate Date

            Dates with Dean are generally very nice. They’re not usually incredibly fancy or high-octane, but they always give you the feeling that they’ve been well thought out. Occasionally there’ll be one that goes over the top. Tonight has been one of those times.

            To start out the evening, Dean had taken you to a restaurant so fancy that it had its own dress code. This meant that you got to spend two hours gazing at Dean in a tux with his hair slicked back. Once dinner was over and you were both in the car, he’d instructed you to change into something more comfortable. He’d changed as well and then driven for about a half hour before parking in front of a movie theater in the downtown section of a tourist town. For the next hour and a half you’d handfed each other popcorn and smuggled candy.

            By the time the movie ended, the sun had set almost completely. Now the two of you are simply strolling hand in hand down the well-lit downtown sidewalk. It’s warm tonight, almost the end of summer, and a gentle breeze helps keep you cool. Little is said, but you’re both completely content this way. Eventually, you reach the entrance to a sizable boardwalk fair, complete with a loopy rollercoaster and towering Ferris wheel. Numerous vendors and fair-game booths line either side of the path, and tantalizing smells entice you further into the fair.

            Dean, of course, treats you to all and anything you ask for, making sure to get enough for the both of you to share. Deep down you both know that eating so much food in one night is going to come back to bite you at some point, but neither of you really cares. Instead, you focus on sampling every greasy, sticky, crap-filled fair food there is. As the night draws on, you move on to the midway and soon learn that any food should be eaten after riding loopy coasters, teacup rides, and especially any ride named after a storm.

            Having had enough of the rides, you and Dean find a park bench in a semi quiet corner of the fair and sit down. You rest your head on his shoulder and lace your fingers between his own, watching the colorful, decorative lights of the fair light up the night sky.

            “So,” Dean finally speaks up. “how was it?”

            “The fair?” You reply. “Or the evening as a whole.?”

            “Both.”

            “Well, aside from puking my guts out after that rollercoaster, I loved it.”

            “Good. I’ve got one more thing planned.”

            “What else can there be?”

            “You’ll see.” Standing, he gestures for you to do the same. “Come on.”

            Trustingly, you take his hand and let him lead you back through the fair. People are beginning to head for the exit as closing time nears. Dean goes against the flow of traffic, leading you directly to the Ferris wheel, the only ride on which you haven’t been.

            “Dean, they’re shutting it down. The whole fair is closing.”

            “Just trust me.”

            And you do. You let him take you right up to the wheel. The ride operator does nothing to stop you as you both climb into the first car. In fact, you think you catch the employee give Dean a subtle thumbs-up. With the lap bar down, the operator gets the ride going. You’re the only people on the entire contraption.

            The wheel rotates twice, slowly, taking you up dozens of feet in the air before swooping back down. On the third round, the Ferris wheel shudders to a halt, leaving your car dangling from the highest point. Confused, you lean over the edge and peer down at the operator who appears to be doing nothing to solve the issue.

            “Technical difficulties?” Dean asks.

            “Yeah, and no one is doing anything.”

            “I guess we’re stuck for a little while, huh?” He flashes you a wink.

            “You say that like it’s a good thing.”

            “Maybe it is.”

            “Why? It’s not like you planned this. Wait, did you plan this?”

            He just shrugs.

            “You did, ya idjit!” You shove him playfully. “I knew I saw the operator give you a thumbs-up!”

            “You’ve caught me red-handed.” He raises his hands in defeat. “Can you bring yourself to forgive me?”

            “Only if you tell me why you did this.”

            “That’s an easy one. I wanted some time alone with you.”

            “You’ve had that all day.”

            “Not like this. Not in the middle of a closing fair under the night sky where everything that drives us crazy is fifty feet below us.”

            “I guess you have a point. So why did you want this alone time?”

            “Because I want to ask you something.”

            “Oh?” Curious now, you shift to face him in the seat. “What might that be?”

            “I gotta tell you a story first.”

            “Okay.”

            “So a few years ago, I met someone. This person was positively gorgeous, and lemme tell you, they could kick some ass, including my own. Not too long after that, I accidentally fell in love with them. Best decision I ever made.”

            “This sounds familiar. Where’s it headed?”

            “It’s headed,” Dean reaches into his pocket. “right here.”

            He pulls a small white box from his pocket, concealing it in his hands as he holds it out in front of him with his entire body emanating hopefulness.

            “(f/n) (l/n), will you marry me?” He opens the box to reveal an elegant engagement ring.

            Surprised, both of your hands fly to cover your mouth. It takes you a moment to finally reply with a nod of your head.

            “Yeah.” Your voice shakes as you nod vigorously. “Yeah, I’ll marry you.”

            He breaks into a smile and then carefully slides the ring onto your left ring finger. It’s a perfect fit. You lean in to kiss him, putting all of your love into the moment. Throughout the kiss, one singular, wonderful thought keeps running through your head.

            You are going to marry Dean Winchester.