I think not many men watch supernatural and understand it. Like yes you all harbor your crushes on Jensen ackles. But why is that? Why does every boy think "dean is better than Sam,"? (An altogether different argument about the fact that the show is about both Sam and dean and if you pick a side then you're not gonna understand it) Anyway, I think it's like with American Psycho. Boys see dean and idolize him even though the whole point is dean's masculinity is toxic. It's a facade. His real feelings– beside womanizer, soldier– are deemed "feminine" by himself. This is not healthy behavior and you as the audience must recognize this. Sam, wearing his heart on his sleeve, being a normal guy, is compared to this caricature of a person, thus making him seem "weak"
I just think that's what happens when u consume media on a superficial basis. You think Patrick Bateman is cool, you think dean Winchester is perfect.