Disclaimer: As may be inferred from the presence of one Susan Ivanova, this is a work of fiction and does not purport to be a factual representation of Rachel Maddow's life. Ivanova, meanwhile, was created by J. Michael Straczynski.
Notes: This scenario is ripped off from 
bessemerprocess' wonderful subconscious, and is a comment fic that outgrew the comment box. Began 07/13/09; finished 07/13/09; posted 07/13/09.
Feedback: Rachel@fangirl.nu or comment on livejournal.
Rachel knows three things about the woman: that she is beautiful, that she is sad, and that she keeps ordering vodka. The last thing, Rachel cannot understand. The woman likes to drink, or needs to, and either way, vodka, when it tastes like anything, tastes like rubbing alcohol smells.
One of the benefits of owning your own bar is that no one can fire you for pissing off the customers, so the fourth time the woman comes in, Rachel ignores her order.
"Excuse me," the woman says, pushing a glass of reddish liquid back towards Rachel. "I asked for a double vodka rocks."
"Oh! I'm sorry." Rachel's practiced this more than once. "Well, please, enjoy my mistake on the house."
"No, thank you."
"Not even a sip? I think you'll like it. It's my secret sauce."
"Your secret...sauce," the woman repeats, her amusement not quite repressed.
"You know the Colonel, with his eleven secret herbs and spices?"
"Which colonel?"
"No, huh? Well, this has Bénédictine and Chartreuse, and that's at least a hundred secret herbs and spices. Add some rye and you're in purgatory."
"Excuse me?" Any hint of levity is gone.
"That's what the drink is called: a purgatory. And, if you don't mind my saying so—"
"I mind."
"Ah." Rachel almost, almost stops, but ministering to customers is her prerogative as a bartender. "The thing about purgatory is, it's a temporary state, and whether you're trying to get into it or get out of it, this'll do the job as well as your vodka rocks, only with...taste."
"Double vodka rocks," the woman corrects. "Now."
Rachel shrugs, takes back her purgatory, and complies.
The woman doesn't come in for awhile after that. Rachel starts to think she won't come back at all. She's wrong.
"Vodka, straight up." The woman looks like she'll pop Rachel if there's any funny business.
"Hey," Rachel says as she pushes over exactly what the woman asked for, "I think we got off on the wrong foot last time. I'm Rachel."
"Susan."
"Susan," Rachel repeats, liking the sound of it. "So, Susan—"
"You're chatty, aren't you?"
Rachel mimes locking her lips and throwing away the key. That night, and the next three times Susan comes in, she serves her all the vodka she asks for, without comment. The fourth time, however, she resumes her evangelical mission.
"I want you to try something."
If Susan had hackles, Rachel would have just seen them rise. "And I want my drink."
"Just listen." Rachel picks up the cocktail shaker she set aside to chill, pours out half of the ice, and strains out the water that's collected. "Rye," she narrates as she adds it to the shaker, "vermouth, and bitters." There is the slightest emphasis on that last word, but if the purgatory had been a little on the nose, surely Susan can find nothing objectionable about Manhattan.
Rachel shakes until her hands go numb. She dumps the ice out of the martini glass she's prepared, strains the cocktail into the glass, and decides not to garnish it. She holds it out to Susan. "The Manhattan. A classic."
Susan stares at it. "If I drink this, will you leave me alone?"
Rachel nods dumbly. It's a lie, but it counts less if you don't actually say anything.
Susan sips, and sips, and sips until the Manhattan is gone. "I don't hate it," she pronounces, and Rachel smiles so hard her face might break, "but I want another vodka."
Rachel thinks about cautioning her to slow down; that, too, is a bartender's prerogative. Instead, she hands over another vodka rocks: not straight up, and not a double, because Susan is in a pretty good mood tonight. That's why Rachel ventures, "So."
Susan rolls her eyes. "So, what?"
"So, why vodka?"
"I'm Russian."
That's actually a pretty good reason, but it doesn't mean she gets a dispensation. Rachel, after all, is a mean dork about drinks. "Huh. Now I know five things about you."
"Remind me again why I keep coming here."
"That you're Russian," Rachel continues heedlessly; "that you like vodka, which is part of being Russian, I guess; that you don't hate Manhattans; that..." Rachel's courage fails her.
"That's two and a half things," Susan observes.
"I'm afraid I don't count well." Having aborted her frontal assault, Rachel tries a flanking maneuver. "You know why I drink?"
"I get the feeling I'm about to."
"I like making drinks—simple things done well. I like the way they taste, the interplay of flavors: pepper, cardamom, citrus. But you drink vodka."
"Mm," Susan agrees.
"I also like the alcohol," Rachel continues when Susan does not elaborate. "The way it makes things go...soft." She looks at Susan obliquely. "Sometimes, people tell me what they're softening up."
"I'm not Catholic," Susan says dangerously, "you're not a priest, and this isn't confession."
Rachel holds up her hands. "Thank God for that." She tops off Susan's glass with her finest vodka. "I'm sorry. I shouldn't push."
"Not if you want my business. There are other bars, with less nosy bartenders."
"But they don't mix as well as I do."
"But my drinks don't require mixing."
"That's why I keep trying to convert you."
Susan almost, almost smiles.
"I remember the fourth thing," Rachel says, "that I know about you." She isn't nervous at all when she says, "You're very beautiful."
Susan's eyebrows rise. "Okay."
"And the fifth thing: you're very sad."
"And the sixth thing: I'm leaving."
"No, the sixth thing is, you're not Catholic."
"The sixth thing is, you're driving me crazy! Good night!"
But good night is not goodbye. "Seventh thing," Susan says the next time she comes in: "I think you're all right. Now give me one of those rye drinks."