A/N: Hello loves! This story is my second story written for the A Slytherin Walks Into A Pub Fic-A-Thon hosted by Draco's Den! My first story was called Classified and it's a Slade Wilson (Arrow) and Bellatrix Lestrange story.

The point of this event was to select a Slytherin and then give a few other fandoms where the admin team selects a character and the Slytherin meets that character with at a pub/bar. Outside of that prompt, everything else was up to the author.

Let me know what you think!

Love always,

Pansy looked at the man sitting at the end of the bar. She had heard rumors about the man who owned this bar since she moved to the Upper East Side, but she had never met the Bass heir. Blair and Serena had told her stories after stories about their experiences with Chuck growing up and going through school, and she had an image of what he looked like in her mind.

Tonight that image was becoming a reality as she watched woman after woman flash their smiles in his direction and seemingly get shot down. She couldn't hear the conversation from her seat, but Pansy could make a good guess as to how it was going. Something was bothering the younger Bass, and with the whiskey coursing its way through her veins, she was going to find out exactly what it was.

Lifting her glass to her lips, Pansy tilted her head back as she downed the last of the drink and gently placed the empty glass on the bar as she hopped off her barstool. It was her turn to get a little flirty this evening.

"Hey there, handsome," Pansy hummed, placing a gentle hand on Chuck's shoulder as she took a seat on the empty stool beside him.

"Can I help you with something?" he mumbled, staring intently at his hands as he spun the glass around in his fingers.

"Aren't you going to say hello?" she asked, pressing on his shoulder to force him to turn in his direction. The grimace on his face brought a smile to her lips.

Chuck took a moment to look the insistent woman pestering him up and down. He noticed some similarities between her and another brunette he used to be quite fond of, but at the same time, she had a spark of her own. Her attitude was what impressed him the most, however. "Hello."

Pansy smirked; he was starting to cave, which meant she had him right where she wanted him. She extended a hand to him. "The name's Pansy Parkinson, and you are?"

Chuck looked at her hand a moment before setting his glass on the bar and taking the hand extended to him. "Chuck Bass, but I'm sure you knew that already."

"Why would you assume that?" Pansy replied as she flagged down the bartender to bring her another drink.

He turned his attention back to the drink in his hand. "Because you still chose to approach me after watching countless others get turned down. You must think you're something they most certainly weren't."

She looked at him for a minute with her jaw dropped. He had some nerve on him to speak to her in that way. It wasn't like he was anything that she should be impressed by. She was intrigued by the challenge presented to her by watching all of those women getting shot down. And yet, here she was practically shot down as well.

"Why are you such an ass?" she blurted out after a few minutes of silence. Pansy crossed her arms over her chest as she waited for an answer.

"I didn't mean what I said. There's a little bit of truth in everything, but I've always been a compulsive liar," Chuck said, shrugging his shoulders as he lifted his drink to his lips. Taking a sip, he returned the glass to the bar and turned to face Pansy. "Obviously, something I said struck a nerve with you."

"Obviously," she hissed, narrowing her eyes at him. "But how am I supposed to know whether what you've told me is the truth or a lie?"

"I guess you can't," Chuck replied, chuckling to himself. "So, how did you know who I was?"

"I'm friends with Blair and Serena," she replied, lifting her glass to her lips. "They warned about you."

Of course, it was Blair. Chuck thought to himself as he shook his head. No wonder she didn't just walk away from him when he didn't acknowledge her the way she wanted at first. "If you've spoken with Blair, then why did you choose to approach me?"

"Because I like a challenge," Pansy said with a shrug. "Besides, I don't take everyone I meet at face value. Buy me a drink?"

Chuck smiled and nodded his head, motioning down the bartender for another round. This was turning out to be an interesting evening after all.