[ Root had asked in the first place for the social aspect -- it's a clear signal that she's open to talking about more than just the job, and he'd taken her up on it, whether or not he actually does any drinking. She gets the vulnerability inherent in raising his mask at all, and she's not going to press on that. (She does have social skills, and sometimes she even uses them for good.)

She's not planning on doing a lot of drinking herself, just sips her old fashioned and uses the glass as a prop to keep her hands occupied. ]

Nope, just curiosity, [ she admits, completely lacking in shame. She's still smiling, amused, swirling her drink a bit. ]

My boss suggested you for this job, and she's... picky. [ That little hesitation was just Root finding the truthful yet privately funniest word possible to use there. ] Usually I can handle things on my own, so when she suggests someone else, they tend to be someone special.

[ In one way or another. Sometimes they're special because they're one of Root's former victims, and the Machine wants her to face that, or because they have a unique particular quality that they need for this specific thing. But they are all special, and anyone who gets the Machine's attention, Root is interested in. ]