23- Date 1

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Dean excitedly put on his sneakers and gave Sam a small forehead kiss. Sam grinned showing his growing tooth and then ran to play with his babysitter. He grabbed his phone and quickly texted Cas that he'll be there in five.

Castiel: Great, I'll just pass by Gabe to give him something. I could possibly be late.

Dean: alright, can't wait to see you 😄

At the restaurant, Dean was sitting at the outside porch, sipping his water as he waited for Cas to show up. Ten minutes passed and Dean started to tap his foot in embarrassment, the what if's starting to fill his mind. It didn't help that the waiter asked if he wants to order.

After around fifteen minutes he texted Cas, in which he got no response. He was starting to nervously sweat as he glanced around. He was ready to cry.

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