Sam decided to take you to the fair on your third date together, hopingto impress you by winning you prizes. It worked out in the end, but not without spending too much money, he wouldn't give you a clear answer on what that number was.

He was pretty good at the shooting games, but he didn’t really manage to win anything for you bigger than a small frog plush. That didn't mean he was going to give up though, that wasn't something a Winchester would do. Although, if his brother could see him now... he'd never hear the end of it. He walked with your hand in his, seeing how you kept eyeing a giant stuffed animal. He didn't say anything, but he made a mental note of it for later.

As the night went on, he led you around the grounds, buying you some souveniers and food. Both of you sat down to enjoy your meal before you needed to use the restroom. The nearest bathroom was a little further away than you'd initially expected. But when you came back to your spot, you saw Sam, with a big goofy smile on his face. And a giant stuffed elephant sitting next to him, along with another small frog plush that was identical to the one he had won earlier.

You'd appreciated the gift, but you couldn't help wondering how much he had spent on you. Not just to play these games, but to win. At first, you didn't ask, enjoying the time you had together. But eventually curiosity got the best of you, and you decided to ask him just how much he had spent.

“Umm...” he smiled sheepishly, looking away from you as a blush creeped onto his cheeks.