Sam set it up
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Dean Winchester is with his brother, Sam Winchester, and his angel, Castiel, at a bar. It's karaoke night and Sam has a plan to bring his brother and a certain angel together. Will it work?
He should be so much more weirded out and upset by these… feelings than he is.
Gabriel’s voice shocks him back into his body and his eyes snap open. “You need some help with that?”
Dean stares at him, uncomprehending, then looks down when Gabriel nods in the direction of his waist. He hasn’t been doing a good enough job of hiding his boner, evidently.
There's apparently a security camera system in the Bunker. Dean is not putting it to good use. (Or he is, depending on your definition of 'good use'.)