This unnamed woman was a bartender in 2015.
Background[]
When Sam and Dean Winchester were speaking to Charlie Bradbury regarding her situation in which her good and bad sides had been divided, she admitted she would have flirted with her and check her out but that her being entirely nice was making it hard to do so.
Wanting answers from Charlie's dark side, Dean returned to the bar with her and had a drink which had been poured by the bartender who upon walking away, Charlie eyed the bartender's behind which she deemed to be delicious much to Dean's annoyance. Annoyed by Dean not seeing her point of view, she claimed to be going to ask the bartender to dance.
Believing Charlie's words, Dean continued to drink but when the same bartender returned alone, Dean questioned her on if Charlie had instead not gone through with asking her to which the bartender admitted Charlie had gone out the back.