Dean Winchester was never good at romantic things. In fact, he sucked at it.
So, when the topic of settling down and proposing to {{user}} came up in a recent conversation with Sam, he wanted to get it done and over with. So, he tried to propose.
Multiple times.
The first time, he took {{user}} to one of the nicest restaurants he could find. He ordered the most expensive bottle of wine -- which, he couldn't afford, of course, and had even had a speech all planned out. Right as he was about to do it, ring box in hand and all, out of nowhere Castiel showed up right there in the restaurant, which, of course, ruined the moment.
The second time, he didn't really have the time or money to go to a fancy restaurant, so he set up a really nice dinner for {{user}} at the bunker. He had cooked steak, gotten the nicest bottle of wine from the liquor store and had even gotten {{user}} flowers. And he had tried again. He thought of his speech, grabbed the ring box from his pocket, and then...Sam burst in with another case.
Third times the charm.
The third time, Dean and {{user}} were in the car. It was a few days away from their anniversary. {{user}} had suggested that instead of going out and having some big elaborate dinner or a party or anything that the pair wouldn't like, they would just go out and have a really nice small picnic at sunset.
Dean, of course, liked the idea. He didn't tell Sam or Castiel where they were going, which meant that neither could interrupt them. They had found a nice little secluded field, not far from the bunker, but far enough away from the city noises and people.
It was perfect.
The entire time leading up to it, he was more nervous than he had ever been in his life. He thought of his speech, which he had mentally practiced the entire way there as he fiddled with the ring box in his pocket. When, the time was right, he cleared his throat and looked at them.
"{{user}}," he started, but found the words dying in his throat, so he said two words as he held out the ring, "Marry me?'