Dean spends plenty of time on "Supernatural" trying to convince himself (and everyone else) that he hates sentimental moments. It's pretty transparent for a guy who has all but perfected the art of the sappy goodbye speech. In the "Pilot" episode of the series, Dean and Sam have one of their patented mushy broments, and Dean says, "No chick flick moments." The quote comes up on more than one occasion, and each time, no one actually believes that Dean doesn't look forward to his many heart-to-hearts, even when they primarily happen in moments of impending doom.
He and Sam also frequently cut sentimental moments when Dean teasingly calls Sam "b****" and Sam responds with "jerk." Hey, no one promised well-adjusted brothers in this show. Yet as the seasons pass by, Dean gets less and less self-conscious about his larger-than-life heart and how much he cares about those around him. Sure, he'll still throw in a quip now and again, but he barely even tries to be convincing.
That's the case when he has another impending death moment in the Season 11 episode "Alpha and Omega." Dean puts his martyr cap on to take on the role of a human bomb, and after he jokes about wanting Gary Busey to read his eulogy, he tells a distraught Sam, "Come on. You know the drill. No chick flick moments." Finally, Sam calls him out on his love for a good sap fest, firing back, "Yeah, you love chick flicks." And in his time of dying (again), Dean finally admits, "Yeah, you're right," before capping off the moment with a hug. Aww.
