Dean
When Alex warned them he wasn't kidding, the entire meal was spent with there sounds of laughing as Leo Walker kept joking and recounting past events which always led to one of the Walker siblings blushing. Dean was amazed because even though he had arrived home from a long day of work, he still had the energy and the want to spend time with his family and enjoy it. And the fact that he included Dean and took the time out to elaborate on each of his stories made him feel welcomed and honored to be able to see this side of their family.
Alone they were serious and intimidating but together, if they allow you to see it, they are filled with laughter and joy embracing each others company. The way a family should be.