Dean-
You two had finished a hunt that no one came out of unscathed. After washing up at the bunker you and Dean decided to go for a drive. That always seemed to calm you down before turning in for the night.
You and Dean pulled over to the side of the road and got onto the hood of Baby, laying back, holding hands, and watching the stars come out.
"Y/n, can I ask you a question?" Dean turned so he was facing you.
"Mmhmm." You turned, curious. Dean slid off the hood and held his hand out to help you get down. Once your feet touched the ground he kneeled and pulled a small box from his pocket. Your heart skipped a beat and your mouth formed an 'O' shape.
"I know that the world we live in is messed up. With our line of work we don't know which day will be our last, but, I do know I want to spend the rest of my days with you. Will you marry me?"
He opened the box to reveal a beautiful antique looking diamond ring.
"Yes!" You managed to choke out the word, nodding quickly. Dean's face lit up as he slipped the ring onto your finger and came back up to a stand, pressing his lips to yours.
Sam-
It was your three year anniversary of dating and you woke up to find the spot next to you empty. Sighing, you slid out of bed and changed into a suitable outfit for the day.
You walked into the kitchen to find that Sam had prepared your favorite breakfast, only, he wasn't in the kitchen. But beside the plate, there was a note.
'I made this specially for you. Enjoy! Next find me at the place of out first meeting. -SW'
You munched on your breakfast thoughtfully. You had met actually pretty close to the bunker, at a park that you ran into him on a hunt.
You hoped into your car and drove to the place. But once you got there, you only found Dean. He rolled his eyes giving you flowers and a new dress.
"He told me to send you to the first restaurant you went to for a date. Not a diner, but a restaurant."
You drove back to the bunker to change into the dress, assuming that was what he would want you to wear. It fit perfectly and looked beautiful! Setting the flowers in a vase, you went back to your car and drove to your first restaurant date. And then you saw Sam, sitting at a table reserved for two in a nice tux and a tie that matched your dress.
"Y/n, you look beautiful." He stood up and pulled out your chair.
"You don't look bad yourself either," you chuckled. A waiter came over and took your orders and while you waited, you noticed Sam kept shifting nervously.
"Y/n, I just wanted to say that these past three years with you have been the best in my life. You make me feel so happy and I couldn't imagine anyone else but you at my side. So, I guess what I'm saying is, will you marry me?" He got down from his chair and knelt in front of you, pulling out a velvet box and opening it to reveal a simple, yet gorgeous, diamond ring.
The people sitting around you waited in silence for your answer.
You nodded, unable to get the words out as tears brimmed your eyes. Sam slid the ring onto your finger and you kissed passionately, causing everyone else to erupt into cheers.
Castiel-
You and Cas were relaxing at a beach in Cancun, Mexico. You were in your favorite swim suit trying to soak up some sun and Cas was in a pair of black swim trunks... and his trench coat.
"Y/n," he said, suddenly turning over and grabbing your hand, standing up. You stood also and met his gaze.
"What is it, Cas?"
"Out of the years we've been together, you helped me see love. I can't imagine loving anyone but you. You helped me open my eyes and see the wonders of the human world and helped me many times."
You blushed.
"Will you join me in the sacrament of holy matrimony?"
He dropped to one knee and pulled out a ring from his trench coat. It was stunning with a sapphire in the middle. People around you stopped and pointed, causing you to blush more.
"Yes!" You tackled him and gave him a kiss. When you two got up he put the ring on your finger.
Gabriel-
You were on a hunt with your brothers, tracking down a pair of Vetala. You had already killed one of them, and the other was in an angry frenzy. She knocked out Dean and advanced against you, knocking your blade out of your hand in the battle. Just as she was going to sink her teeth into your neck to paralyze you, you felt someone grab your hand.
You found yourself under the Eiffel Tower with Gabriel standing in front of you. He lurched forwards and gave you a kiss.
"Thank goodness you're okay," he sighed, stepping back.
"Thank you for saving me," you chuckled. "What are we doing in Paris?"
"First place I could think of. Let's have dinner."
"But my brothers-"
"They're fine. I had Castiel smite the vetala and bring your brothers back to the motel while I saved you. I also told him to tell your brothers that you were fine. Now, follow me."
Gabriel escorted you to the elevator and they took you up to the restaurant. You two went to the bathrooms and he conjured up a dress for you to wear, this being a fancy place and all.
In no time you were seated and munching on your dinner.
"I remember our first date here," you sighed, looking out the window and to the people walking below. When you turned back, you saw Gabriel on one knee, with a beautiful emerald ring in hand.
Your heart skipped a beat.
"I could have lost you today, if I hadn't got to you in time I would have never forgiven myself. How about we stick together from now and on? I love you, Y/n. So what say you, veux-tu m'épouser?" He gave you a hopeful smile. The dinner guests around you chattered excitedly.
"Oui," you said, returning the smile. "Je vais vous marier." Gabriel smiled and stood up, giving you a soft kiss before pulling away to place the ring on your finger.
(Translated from above- Will you marry me?
Yes. I will marry you.) Gabe obviously had help from Balthazar.
Crowley-
You were just laying around, bored, when Crowley seemed to waltz into the room.
"Y/n, love, lets have dinner."
You shrugged. "Sure."
After getting into your favorite dress you met Crowley in the kitchens were he had set up a nice table. You two ate in silence, picking up small talk here and there.
"So, fancy dinner, what's the occasion?"
"Because I love you," he responded.
"Good enough reason for me, I love you too."
"I also have a very important question to ask you."
"Which is?"
"Will you marry me and be my queen?" He pulled out a ring, the in the middle was a diamond flanked by garnets.
"Of course!" you smiled, getting up to give him a kiss and letting him slide the ring on your finger.
Charlie-
It seemed like any other day, until you turned on the news. Today was the day that same sex marriages were legal in all fifty states! You let out a shriek of happiness but then quieted yourself.
You and Charlie had been wanting to get married for a while, now you just needed time to propose to each other!
You and Charlie seemed to be tip-toeing around each other for the rest of the day. You wondered if she saw the news too.
Eventually, you two and the Winchester brothers went out to get dinner. Well, you were going to get dinner until the Impala broke down.
"Dammit!" Dean yelled, pulling over and getting out of the car. You and Charlie snickered and went out for a walk, letting Sam and Dean handle the repairs.
You two were holding hands and went into the forest nearby. Of course you tripped over a stick and brought Charlie down with you. You both looked into each other's eyes and knew exactly what the other was thinking.
"Yes." You both said at the same time.
The next day you went out shopping for matching rings.
Lucifer-
Who knew Lucifer was such a romantic?
You two had arranged to go out on a date for a while. So, he took you out to a simple lunch and you two explored the world until dinner. He had managed to get all your favorite foods to a secluded meadow. You two had a beautiful picnic and just talked.
Then the sun went down and the stars came out. You, loving photography, took out your camera in hopes of getting a good picture of the milky way band. What you didn't know was that Lucifer was making meteors pass in certain directions and making sure your camera caught their streaks.
Then, once he was finished, he asked for your camera. He overlapped the pictures into one until the words 'Will you marry me?' showed up on your screen, all formed by the pictures of the meteors. He gave the camera back to you and let you take a look.
"Oh my god," you whispered, then turned to Lucifer excitedly. He pulled out a ring and raised his eyebrow. "Yes!"
For Gabriel's, I decided to add French because, why not? You're in Paris. You probably took French classes like Sam took Spanish, no biggie. And Gabe, he's an angel, he probably knows every language. Or, as I said, probably had help from Balthy.
And, also I take French so I had to... But now you know how to propose in French! Whoo hoo!