"There are probably many things that I could picture you in, cowboy boots are not one of them" Mika replied back to Dean in between mouthfuls of pizza as she tried to not go down memory lane in her head. Sure, the time together where there wasn't drama going on, the peace that was between them was nice and very much welcomed by her, but she couldn't help but wonder when that would begin to falter. Then came the first awkward question of the night which made her pause her eating, gulp down her mouthful and pause to think about her answer. She eventually nodded and glanced down before back up at him, "Yeah, heard from him a couple of days ago" she replied and it wasn't entirely a lie either. It had been a couple of days and no doubt she would be in great shit with him for it, as she always promised to check in daily. She knew how protective Bobby was of her and rightly so, he was her uncle after all. Dean just didn't need to know that. 

"Should probably check in with him at some soon, see how he is" she added, but her eyes glanced downward and to the left slightly, which she tried to cover up by grabbing another slice of pizza. She thought it was a good 50/50 chance if Dean would pick up on her body language but it was a risk she had to take. "What about you? You heard or spoken to him lately?" she asked him back. 

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Sam wondered why Anna was narrowing her eyes at him but when she spoke out her assumption, he went wide eyed slightly and nodded. "Yeah..." he replied, not knowing what else to say but it seemed Anna had that under control as she contiued to speak excitedly. "I..I'm not sure I can tell you what he does. He had leads, I think, he kinda doesn't tell me much to be honest" he shrugged, using his can of soda as a get out for talking much more.