He scowled a bit when Dean ordered him a shot against his word, eying the drink with a disapproving look. The last time he had gone on a drinking binge, Sam had ended up getting knocked out cold in the middle of a bar and tossed into the parking lot in front of his truck. Faith wasn't exactly here to navigate him home this time around. And Sam was so tired of getting bruises all over his face.
Besides that, the demon was still out there somewhere. Watching and waiting, probably. He shook his head and tapped at the shot glass with his hand, doing his very best to fight off the temptation that Dean had thrust before him.
At Dean's words, he lifted his gaze and peered off toward the woman he was gesturing toward. His eyes then ticked off toward the one that Ruby was speaking about and he shook his head. Nice. Real nice. He was sitting in a bar, with someone who probably hated him on one side and his determined to drink away his problems brother right next to him. A couple months ago and he'd be mortified at the idea of drinking with a demon who was trying to hand out fling advice. Now he was just tired enough to let it go. Even if it did weird him out a bit. Shaking his head, Sam pointed toward the redhead. "We're talking Dean's type, Ruby, not yours. And I'd say go with the FBI speel, you've already got the badge and everything."