I agree with you so much here. The song choice was odd for Supernatural, but coming off the heels of an episode where we see Dean admit to being a Taylor Swift fan made me pay even more attention to the musical choices. And to use a song so strongly linked with the gay community, well, what connections did they EXPECT us to make?
I wanted to add something too. I thought the episode was a pretty crappy filler until I looked closer. First of all, the three students that died all had aspects we associate with Dean: a vehicle they love, being good looking, and loving music. They all were killed, possibly indicating the dying off of Dean’s old way of living, while the only one who lived was the one living with regret. The character with emotional, caring depth who mirrored Dean’s current emotional status was the one that lived.
And the only reason the “monster of the week” was defeated was because someone loved him, and brought him back to himself.
Then, you have the change in Dean’s habits. He went from trying to live like Sam to trying to live in an exaggerated form of how he used to be (junk food and women). But neither of those ways work because that just isn’t who Dean is.
At the end, like you said, we get that whole speech from Dean. When he said that the answer wasn’t out in the world and was instead IN HIM, I nearly fell out of the chair. Because yes, Dean, the answer IS in you if you’d only admit it, and it has literally been staring you in the face for years. You just have to open yourself up to allowing something good to happen, just like you’re slowly opening up to who you really are this season.