Esme Stirling
Esme turned back to Dean with a smile when he fiddled with her hair and agreed to the walk. She then looked over at Sam and Madison when Dean asked them for approval, which he quickly got from Sam. She was happy about his approval. She then looked at Madison as Dean slid himself out of the booth and held a hand out to her. At Madison’s approval, she smiled and gave a laugh at her comment about Dean. “I’ll try my best.” she said as she slid across the booth seat.
Another laugh escaped her at Dean’s raised eyebrows and scowl to Madison. She even caught the rolling of his eyes. She was going to ask Madison if she was sure, but she saw she didn’t need to as Madison spoke again and took Sam's hand. She was happy to see that she trusted Sam enough to be alone with him. She was also glad that she didn’t have to worry about her. She could see that Sam would keep her safe while she and Dean talked. “Well, you two have fun.” she smiled.
She looked at Dean and took his hand, giving it a gentle squeeze as she let him help her up. “Oh, if my cheesecake gets here before we get back, please don’t eat it.” she said in a joking tone as she looked back at them with a grin. “Shall we?” she asked, as she turned back and looked up at Dean. She had almost forgotten how tall he was and how short she felt standing next to him.
Sam Winchester
Sam looked over at Madison as he looked at her and gave a small laugh. “I’ll try my best to answer your questions.” he said before she looked at Esme. He looked at Dean as spoke and gave a laugh. “I wish you luck with that.” he chuckled. “It won't be easy.” He saw Dean’s look at Madison and caught the eye roll. He gave a look of his own that said ‘I know’ before looking back at Madison. When she took his hand, his eyebrows went up a little. He wasn’t expecting such a gesture from her in the short time she had known him.
He didn’t move his hand though, he gave her a smile before catching Dean’s weird stare at her. He shrugged his shoulders to Dean, then watched Esme slide over and take Dean’s hand and leave the booth. He gave a laugh at Esme’s joke. “Don’t worry. It’ll still be here if it gets here before you get back.” he told her. “Now you two get going. You two have plenty to talk about. We’ll be fine.” he added. Using his free hand, he gave them a shooing motion to get them going and out the door.