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[Text: Griff] Will do, as funny as his sneezing fits are.

[Text: Griff] What did you name your cats by the way?

Uncharacteristically, Dean had decided to be a gentleman regarding a woman he was interested in. It wasn’t to say he wasn’t a gentleman to all his one night stands, but this was different, very different. Plus, when it involved a protective mother who knew how to use a gun, Dean had reason to be on the proper side.

The elder of the Winchester brothers walked into the Roadhouse, looking for Ellen and finding her leaning on the bar. 'Son of a bitch, was she expecting me?' he wondered, eyes widening for a moment. Dean cleared his throat, "uh, hey Ellen. Nice to see you," he said, feeling like he did back when he was 16 and at Sonny’s, talking to the girl about the dance. Asking for permission, or rather to not get shot, to ask Jo out was one of the most nerve wracking experience he’d ever had. Rubbing the back of his neck, he met Ellen’s eyes. "I was wondering if I could take Jo out to dinner, and I mean a proper dinner where they have candles and a snooty waiter who has too much gel in his hair," Dean asked, realizing the second part of what he said was too much. 'God, so much for my reputation as being smooth. At least she isn’t the one I’m actually asking out,’ he thought, anxious to hear Ellen’s answer. He knew if Jo had overheard, she would have given the “I’m not a little girl” speech to both of them.

~~~~

Ellen was taking a break from organizing the orders for next weeks shipment, for the Roadhouse, when Dean walked in. 

She picked up her beer taking a drink from it and setting it back down on the bar as he approached. "It's been awhile, Dean. Good to see ya. How's it going?" She replied to his greeting.

Ellen looked the boy over as he headed her way. Was he nerves? In all her time she had never known the Winchesters to be the nervous type. His nervousness made her feel a bit uneasy. If a Winchester was nervous something real must have happened. " You alright there? What's got you so riled?" She questioned as he awkwardly rubbed the back of his neck.

Ellen was about to question him further when he spit out his request. She rose an eyebrow and opened her mouth to say something but thought better of it and closed her mouth again. She stared at the Winchester, eyes upon him, her gaze fixated on his face. "Did I hear you right, Dean? You want to take my Jo out?" She asked just to be sure she wasn't hearing things.

She gave it some thought before she let out a breath, mostly of defeat. "I guess it was only a matter of time." She softened her gaze. " I just never thought you would actually work up the nerve to ask." She stated more to herself than to him. "I'll tell you what Jo would say, she'd tell both me and you that she's not some little girl who needs her mother's approval. We both know it." Ellen told him.

She let out another breath and tilted her head giving him a slight nod. "You know, I respect you coming here and asking me first. Even if Jo doesn't care what I think."

"You have my permission." She told him."But Dean?" She paused before adding, "If you hurt my little girl, It won't be just your head you'll be missin'. If you catch my drift." She warned.

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Singersonlydaughter is great with long replies as well. Bobby's adoptive daughter OC.