When they met.
Dean was a new student and was introduced in history class. After the class, Audrey showed Dean around school. Tiffany beat Dean up at Starbucks after seeing his old notes and texts on his phone. So then Audrey took him to the school nurse.
Dean and Audrey pretty much became friends after that. Dean is starting to like Audrey, not just for his revenge, but is starting to truly like her, more then a friend. (They might become a couple!)
After Dean got drunk at Coco's party, he went a little nuts and hurt Audrey, so now Audrey is avoiding him, acting like she never seen him before in her life.
Support and love <3
After Audrey's parents died, Tiffany had Dean take care of her while she was sad. After she was better, they kissed and now Were all assuming that they became a couple. <3
Well, Dean had to go to the other realm for hunting, he left a note for Audrey saying he couldn't visit her to the other realm because Allegra closed the portals so the demons can't get out. Soo, that was pretty much a breakup.