Pippin had surprised herself by how vehement she was with Dean's bad habits. After chastising him about the mystery treats she'd had to examine her motives. What she'd learned was that she liked Dean. He was a good guy. He lacked impulse controls, and had a foul mouth that would make her mother faint, but she believed she saw something that perhaps he didn't.
Still, the more he opened up, the more she learned about the things he'd done, places he'd been. Pippin was intrigued, but also concerned. She had a big heart. Her brothers told her it got her in trouble, and that she should toughen up. She never did. So after Dean dropped a few info bombs she insisted that they meet for drinks. And talk.
She already had a glass of Jameson straight up when Dean arrived at the bar. "Hey! I couldn't believe my eyes when I saw this bottle. My dad would have happily murdered someone for one."