Dean
He did it, he finally admitted the truth and he couldn't help but steal the moment and take the chance to tell her the truth. He knew it was a risk but he saw what happened when people spent time hiding their feelings, they either spent years apart or in the end get a long waited rejection causing hate to brew and he didn't want either. He much rather told her his truth and find out if there is a future for them if not he would settle and stay her friend and not expect nor hope for more.
After Anna announced her presence she said hello to Dean before dragging Alison away demanding that she needed girl time with her best friend. Dean shook his head and laughed as a startled Alison was dragged away and decided to collect his things and turn off the systems. After collecting his phone from the booth he turned around and jumped in freight not anticipating the unannounced visitor.