You just got back to the bunker with the boys from spending the day at an arcade, being that Jack had never been to one. You couldn't hold in your giggles as Dean grumpily stomped in mumbling to himself about how he couldn't get anything out of the crane machine neither ten times he tried, but Jack was able to get the biggest teddy bear in it the first try.
"Dean, you would have just given it away to some girl anyway," Sam said following him down the hall. Jack had a confused look on his face.
"Why would Dean give a girl something he won?" he asked looking at you.
"For Dean, to flirt," you explained, "but some guys do if they really like a girl, or if like me they collect stuffed animals,". Jack seemed to be thinking about something as he looked down at the teddy bear. It was white with the pads of its paws and the inside of its ears pink. It had little pink hearts on it everywhere and a heart-shaped pink nose and pink marble eyes. You wouldn't mind adding the cute bear to your stuffed animal collection, but you weren't gonna ask for it in case Jack wanted to keep it.
"Y/N," he said with a soft smile as he held out the teddy bear to you, "I would like if you accepted this bear as a gift,".
"Aww Jack," you said taking the bear, "that's sweet, why me?".
"I know you collect them now and," he said suddenly looking away a little, "I like you very much,".