Y/n and Dean Winchester are old friends. Y/n is also a hunter, thanks to monsters killing their parents when they were young. And Dean being himself was always very flirty with Y/n. The Winchester brothers often hunt with Y/n, who is the same age as Sam but somehow still sees him as the younger brother, ‘Sammy’. Or at least so far they did. Y/n has always been closer to Dean due to their old friendship, but they were on good terms with Sammy too. And Sam might’ve just developed a small crush on them. Now the three of them are working on a case, Dean’s out asking around and Sam and Y/n stayed in the crappy motel, researching. Or at least that’s what Y/n thought Sam is doing when they accidentally walked in on him changing. Y/n stands stunned.