and finally ends up dating someone he never knew he would date

Dean swallowed. Was he being serious? Did he mean what he just said? Because if he did… His head was spinning and his heart was beating way too fast. This was doomed to fail.

He felt so out of character.

Cautiously he glanced up and said, "Maybe…I would?"

Cas's eyes lit up. He was looking so cute, huddled on that mattress, complaining about his failure. Dean glanced up again and when their eyes met he gingerly took his hand and leaned in and a joyous feeling flooded his body when they kissed.

Dean smiled. Jackpot.

Sam (spying on them): "Finally."