The Thrill of the Chase

One

Starts in season 5 ep 17, Pulp Fiction episode while everyone is at Finn's birthday party. Some paraphrasing from the episode to help set the beginning scene before going AU. 

"My entire goal in life is to outlive my brother, inherit the family fortune, put all my sisters out on the street and live as frivolously as possible, have numerous wives, thousands of illegitimate children and die completely alone and leave every cent to a parrot named Polly." Robert rants while smirking at Rory across the table.

"That's your entire goal in life?" Rory asks incredulously, staring at the man in the blood soaked white shirt.

"Except for the name of the parrot, I stick to everything I just said," Robert states emphatically.

"You're a fascinating specimen, Robert." Rory retorts with the beginning of a smirk. She is just ready to start to reply when they are interrupted.

"Well, Josie's a lesbian," Colin says, disappointedly.

"You struck out, Colin?" Rory asks, feigning sympathy as Robert laughs at Colin.

"Whatever. Is Lydia here?"

"Yeah, she's here with Patrick, her fiancé," says Robert.

"God, I hate these stupid incestuous parties! It's the same people over and over." Colin rants while taking another drink as Finn comes up from behind him and throws his arm around Colin.

"Who's as drunk as I am?"

"No one since Spencer Tracy died. Finn, are there any interesting women here at all?" Colin asks, his exasperation showing on his face.

"Have you tried Josie?" Finn asks in all seriousness.

"I'm getting a drink," Colin says, storming off to the bar.

"Alrighty. I have to go make the rounds," Finn says, getting ready to move on. "Have I met you yet?"

"Several times." Rory answers with a sigh.

"All right then." Finn states before leaving the couple to it, as they look at each other and smirk.

"So, how about that drink?" Robert asks Rory before they can be interrupted again.

"Nothing too strong?"

"I'll see what I can do." he says with a smile as he walks away from the table heading towards the bar.

As soon as Robert walks away from the table, Logan quickly approaches with his drink in hand, so quickly that Rory realizes he must have been watching the table.

"Hey, Ace. Having a good time?"

"I am, thanks." Rory replies, trying to remain focussed on the dance floor.

"Good. That's good. Me, too. I'm having a good time too." Logan nods as he talks.

"Good."

"Yes, it is good. So I didn't know you knew Robert." Logan asks after taking a deep breath.

"I met him at the Life and Death Brigade gathering. And the poker game." Rory replies with a raised eyebrow, showing that she was suspicious of his line of questioning.

"Oh. Right, right. Well, he must have made quite an impression."

"He just asked me out, is all," Rory says honestly.

"Sure." Logan agrees, as he takes another sip of his scotch. "He's kind of a jerk."

"Excuse me?" Rory replies, shocked that Logan would try this tactic when they were each on separate dates.