Classy

We can look at the text for number 1 - and I do that uh - a lot - see the blog name #Dean Was Always Bi

For number 2 we can look over some points when we got clues from what Jensen thought was going on [regardless of whether they make sense based on his jacting or directorial choices I guess] and get left wondering whether at any point he felt pressured to lie for his career, for self protection, or to protect the narrative from the network: 

2010 - 'We're missing the gay angel' (x) (Season 5 gag reel) (x) “Sorry man, not what the show’s about.” Jared: One of the good and bads about playing the straight [non-comedic] character on the show… Jensen: What wait? I’ve been playing him so wrong

2012 / S8 - Trenchcoat - Jensen talking about how sometimes they change the lines because they're way too gay. Calls Cas a third brother

2012 - "What's Destiel?" Ben Edlund: That’s some weird shit. Jensen: Is this something that you created, Ben? Ben: You don’t want any part of that.

“Don’t ruin it for everyone now” “I still don’t know what the question was. I’m going to pretend I don’t know what the question was.”

2013 @ JIB, re Dean’s reaction to Aaron’s flirting in the season 8 episode Everybody Hates Hitler,  (x)

“And the scene wasn’t written to be that kind of - I mean - It was written to be awkward.  Ben Edlund wrote the - my favorite line in that scene was ‘carry on . citizen’ that was - I almost couldn’t say that with a straight face I was laughing so hard.  But it was - you know - it was comedy. It was a comedic moment in the show and fortunately Dean gets a lot of the comedic moments in the show and it was just, you know, Ben was poking fun at the fact that - you know, how can we make this very kind of manly, heterosexual guy uncomfortable - uh -you know, or  or have him back on his heels and throw him off his game a little bit.”

The thing is - Bedlund and Phil Sgriccia made very clear on the commentary track that THEY saw this scene as a 'romantic comedy kind of fluster' "This potential for love in all places."

Ben Edlund calling the writer’s room a boy’s club in 2013 (x)

Misha Collins telling Destiel fans they aren’t Crazy in 2013 after some executives said they were (x).

2014 Jensen says he was glad there wasn’t much Dean and Cas in season 9  - HA Hah HAH (x)

“I think the whole Cas and Dean thing has gotten out of hand”  “I don’t think there’s anything secret to their relationship even though a lot of people wish there was” REMINDER - that season we got the nightstands acknowledgement and “play him like a jilted lover” and the “he dumped me James” cut and -

I certainly know that Misha and I don’t play that. SIGH. they Ben Hur'd Jensen.

2014 - the fan fiction joke - 10.05

“I didn’t have a positive reaction, The first time in I think 200 scripts I went and sat down in the showrunners office and said, ‘What in god’s name are you doing?! Why? I need to understand why this is happening.’” “[Carver] gave very eloquent answers and did a great job of explaining why we were doing what we were doing, I guess I had been aware of this ‘fan fiction’ for a while and I felt like maybe if I ignored it, it would eventually go away. When I read it in the script that is what I do for a living and is my work—I’m very protective of these characters and the story and I think we have a right to be—I wasn’t angry. I just wanted to understand why and what was the message we were ultimately sending with this script and story. By the end of it, I felt good and it gave me all the confidence I needed. It was better than I could have ever hoped.”

But then there's Jensen in 2015 talking about all of Dean’s bromances. (x)  [gifs at the top] Could go either way - starting to figure it out? or No?

What had changed if anything? the entire Crowely season 10 story line?  This was July 2015 - the same day as the SDCC 2015 panel where Misha talked about Destiel   (x @ 13) Carver and Dabb were there - 

By this time Jensen and Misha were nominated for a teen choice award for best chemistry against various tv couples (and one ensemble cast, but the award nomination did NOT include Jared) .... Misha and Jensen would go on to WIN this award one month after the panel.

At the Panel Rob and Rich ask the question: “You two have branded yourselves as TV’s greatest team since, ... idk who.... Ernie and Bert so.”  [Misha says to Jensen & Jared, half not on the microphone: “I really didn’t expect them to throw us under the bus.”] “are we going to see that continue? Is the Castiel Dean relationship still aflutter and still growing as we move into season 11?”  Jeremy Carver: “Ish.” [mocking from panel ensues] “Yes. Of course. I mean Yeah. Absolutely. Yeah. There’s no doubt.”

Jensen Directs 11x03 and the choreo mimics Goodbye stranger (x)

2016 - Jensen: Dean could have a huntress, but you’d kill her.

Jan 2017 Con the infamous - no hedge - harsh - “Destiel doesn’t exist.” (x)

I would hope that if he knew he wouldn’t have been so harsh with it.  So by that point either he still didn’t know - OR - to him ‘Destiel’ was specifically about internet porn/sex and not like - the potential for feelings / a relationship.  It makes me think about something Misha had actually said, around 2013, “It’s called ‘Destiel’ and it’s about the romantic interludes between Dean and Castiel.” (x)

2017 - jib8 Jensen called Dean a lover of the ladies

May 2017 - After filming the end of season 12:

2018 - Misha confirms he and Jensen have talked about Destiel (x) - also 2018: The Bisexual Dean essay "? No." (Oh god was this really this recent?! I can't deal with this.)

Well. SOMETHING happened in 2019. cuz here it comes

2019 - "Dean has no taste, clearly." 2019 - 'So, tell us just a little bit about what you're most excited to tackle with your character this final season.' "Cas. Just like a full football form tackle."