Casual Date-thing with Octavia

>It is a beautiful evening at the Bannered Mare, perfect for sitting outside and watching the sunset
>So of course you, Anonymous, are inside at your usual table, third from the back on the right, regular as clockwork
>fuck the sun
>you are currently nursing a few scratches from the ferrets and weasels you fed for Fluttershy earlier today
>damn things have razorblades for fingers
>Thank god she thought better of having you feed the bear too
>You hold the beer, your second of the evening, against your scrapes, enjoying the cooling sensation
>the bar is mostly empty
>it's nearly dark outside now
>maybe she won't be coming in today?
>nope, spoke too soon
>a grey mare with conservatively coiffed hair comes trotting in, setting an instrument nearly as big as her in the corner
>the moment it's out of her hooves, she canters up to the bar and sits down on a stool facing toward the liquor bottles
>you've seen her come in like that a few times this week
>and every time...
>yep, a double of gin with just enough tonic to qualify it as "not just straight gin"
>oh, and a lime
>classy
>you polish off your glass and raise your eyebrows as she downs another large gulp
>she's barely halfway through her first when she waves the barkeep over for a second
>that's unusual
>normally you see her nurse a drink and leave after a few hours
>at the rate she's going you'd be amazed if she could stand by that time
>you scratch at a bit of dried blood on your cheek
>maybe you should say something to her?
>You stand up, giving your neck a crack as you wander over in the general direction of the bar
>your glass was empty anyway, and you point at the stool next to the musician while looking in your waitress' direction
>she seems to get the gist of it
>you clear your throat as you approach
"'Scuse me, is this seat taken?"
>the grey mare looks at you sidelong, arching her eyebrow
>then she looks at the entire bar's worth of empty seats
>then back at you
"...Nooo... sit where you like, I s'pose."
>she looks back down into her drink, taking another respectable portion of it
"Awesome! What're you drinking?"
>you give her a smile, which she hesitantly returns
"This would be a gin and tonic."
>You nod, pointing to the fresh mug of beer the bartender puts before you
"Cool. You should try the Spring Pale Ale, it's made out near Appleloosa, they add a little honey in during the brewing process, and then lots of hops to give it that extra bite."
>She nods, pointing to her drink in turn
"Mine's made in the Bannered Mare. Their secret is to add both gin and tonic to it. Trade secret."
>you give her a deadpan stare
>with her Braytish accent and stoic face, you can't tell whether she's being sarcastic or not
>she rolls her eyes, giving you a nudge
"It's a joke, guy. Lighten up!"
>she downs the last of her first drink, pushing it aside and picking up the next one
"Someone ought to be happy around here..."
>she mumbles as she takes a sip
"Sorry, it's been a while since I've heard a joke that didn't start with 'knock knock' around here."
>you explain, blushing but smiling nonetheless
>Ponyville wasn't exactly the stand-up capital of Equestria
>she nods in agreement, and you both take a drink at the same time
"So, you're Anonymous, I take it?"
>you nod
>you'd be surprised she knew your name, but given how many other humans you've seen in Equestria so far, it was an easy guess
"And you are...?"
>you hold out a hand to shake her hoof with
>she blanches momentarily, but puts her hoof in your hand and gives a short, professional shake
"Octavia Melody, a pleasure."
>you commit it to your memory, as best you can with the bit of a buzz you have going
>the two of you go back to your drinks, letting a moment of silence stretch out
"So, erm..."
>you start
>she looks over at you and brushes a few stray hairs from her mane back into place
"What do you call a tiny psychic who's escaped from jail?"
>she blushes a little at the childishness, waiting for you to tell her
>no no, you wait until she asks properly
"I don't know, what?"
>she arches her eyebrow at you again
"A small medium at large. Eh?"
>you give a chuckle
>she rolls her eyes, but it did get her to crack a smile
"Maybe you should stick with knock knock jokes, that was a bit awful,"
>she suggests
"Not my fault all my good jokes can't be told around here,"
>you shoot back
"Oh? Some sort of language barrier?"
"Nah, just don't want to shatter someone's sense of innocence."
"Oh, thank you for sparing my virgin ears,"
>she snarks, taking another sip
>huh
>well let's give this one a try then
"Alright, fine. What's the difference between a prostitute and an onion?"
>she chokes a bit on her drink
>her tail flicks as she recovers
>it takes her a bit to recover, and she holds up a hoof in apology to the barkeep for the mess she makes
"I don't know... what's the difference between a prostitute and an onion?"
"Cutting up onions makes me cry."
>she stares at you, stone faced
>there's a long, drawn out silence
>oops
>too much?
>"Pffffft... Hah! Hahaha!"
>she can't hold her expression any longer, and bursts into a fit of laughter that she tries to subdue quickly
>she covers her mouth with both hooves to muffle the noise
>"Oh... oh you can't tell anyone I laughed at that, that's terrible."
"My fault for telling it,"
>you smirk and polish off your third beer, waving the bored-looking bartender over
>She calms down a bit, taking a deep breath
"Hey, let me buy you a drink as an apology for making your snort that one."
>you order another G&T for her, and a rum & cola for yourself
>the stallion nods curtly, reaching for the glasses
>the two of you sit at the bar together for a while, drinking and swapping jokes
>you nurse your booze, what with the old "beer before liquor" rule
>she manages to put away two more glasses of her favorite poison on top of the two she'd already had
>not bad
>you swap the occasional story, talking about your recent exploits around Ponyville while she explains some of the finer points of the contra-bass
>you manage to get a few more jokes in
>so does she, to your surprise
>"...so then the drummer shouts, 'take away one stick and tell him to wave it around!'"
>you shake your head, laughing more at how funny she finds herself than the actual joke
"Glad to see you're in a better mood now than when you came in"
>you offer, the both of you still chuckling
>"Hah, meeeee too. Who says you can't drink all your troubles away?"
>you raise your glass in a cheers to that sentiment
>she clinks hers against yours, both of you downing the last bit of your respective drinks
"If you don't mind my asking, what did have you so down at the start of the night?"
>you look down to see another full glass each in front of you and your new drinking buddy
>she waves the question off nonchalantly
>"Oh, you know, life's little slings and arrows. Crazy roommates, obnoxious landlord, job hunting..."
>you give her a confused look
>didn't she say she was an orchestra member?
>you ask as much
>"Ex. Ex-bass player for the Canterlot Symphony Orchestra. They suffered a huuuuge blow to the budget after some manic pink mare abs'lutely ruined the Gala last year, so they're 'taking a break' while they recoup some money."
>you wince
>you wince harder once you realize that you probably know where that mare lives
>perhaps you'll leave some details out when it comes to stories about Pinkie
"So... what're you doing until then?"
>you shift uncomfortably in your seat, not wanting to push the issue
>"Working for scale at the commun'ty theater here'n Ponyville,"
>she shrugs, utterly failing to hide her contempt
>all at once her mood shifts, as though she's resolved that she's done feeling that way
>"But! Without the hours of practice I'd normally hafta put in, I c'n do whatever I want after work. I can come to the bar, enjoy not bein' at home, avoid everypony who might recognize me in town, talk with a cute funny gentleman, get thoroughly pickled, embarrass myself n'front of said gentleman, and still make it home in time to sleep and be ready for the next day!"
>if it weren't for the blush creeping across her face, you probably wouldn't even have noticed what she'd said
"Wait... huh?"
>"Right, well, I think I've done everything on that list for today, so--"
>she stands up suddenly, startling you out of your train of thought
>must've startled her too
>you hold out a hand to help her back to her hooves from the floor
"You alright?"
>you can't help the ear-to-ear grin
>"Yes, yes, yes, yes. Yes. Fine. Well, it was a pleasure Anonymous, I'll see if I can handle m'self like less of a dolt next time--"
>you put a hand on her back and stop her from leaning too far over
>you thought it was kind of strange she could drink like a fish without looking destroyed
>turns out she's just the most straight-faced shit-faced pony you've ever met
>still, anyone who can look slightly bored while struggling to stand upright deserves a medal in your book
"You, uh, want me to walk you home?"
>she gives you a look that's somewhere between sultry and patronizing
>"I think I c'n manage. I do thank you though.  Sincerely."
>you lift your hand from her back and watch as she lists to her left
>you bring her back to center and shake your head
"I'll rephrase: I'm going to help you walk home. Let me pay the tab real quick."
>she looks almost insulted, but relents after a few seconds of your pro tactic of "not letting a mean look dissuade you"
>nodding, she takes a few steps for the door, before opting for a seat instead.
>the bartender whispers a thanks for helping her get to where she needs to be
>good guy, that one
>collecting the little pony and her massive instrument, the two of you start for the door, her leaning heavily into your side
"So... you wanna talk anymore about that whole 'my life is in a downward spiral' thing?"
>"Do you legitimately want to hear me moan about how unbearable my life is?"
>you accede that point
>but hey, we've already gone this far
>can't hurt
"Eh... if it'll help."
>she bites her lip for a second
>"I just hate that I am where I 'm, I guess,"
>she volunteers, keeping most of the slur out of her voice
>"It's cosmically unfair, y'know? Being taken away from a life you're so familiar with and being forced to make do, hoping one day you'll get back."
>you nod as though considering that for the first time
"Eeyup."
>you give her some time for the realization to sink in
>...
>nothin'
>might be the funniest joke she said all night
"Well, don't worry too much. Things always work out alright, don't they?"
>she gives you a derisive snort
>"Right, right. I've got a party animal roommate--"
"Who pays more than half your rent--"
>"A landlord who hounds me for every cent I make--"
"And lets you live there week-to-week so you can take off easy when you land your big job--"
>"A bunch of incompetents to play in the pit with--"
"That are getting more popular with your name as a draw--"
>"And a drinking problem--"
"That gets you out of the house to socialize--"
>"yes, in a bar with a bunch of strangers--"
"where you met a cute, funny gentleman to walk you home."
>you stick your tongue out at her while she blushes at you calling her on her earlier slip of the tongue
>you're pretty sure the silence means you win that one
>"...Dirty pool, sir."
"Admit it, it could be better, but is this all that bad?"
>she rolls her eyes, but she's still blushing a bit
>she just stays quiet, leaning against you as you make your way towards her place
>you aren't sure how much of that is her using you to keep upright anymore
>you walk in silence, hand on her side, holding her close to you
>you aren't sure how much of that is you trying to keep her upright anymore
>eventually you reach her door
>she seems reluctant to leave your side
>so, wordlessly, she sits down on the steps up and beckons you to join her, her leaning against you, both looking up at the stars
>"Uhm..."
>she starts, not taking her eyes off the sky
>"Thanks, Anonymous. For walking me home. And for listening. And for arguing with me. And making me laugh."
>you shrug
>someone had to do it
>the two of you sit there a bit longer, only moving to point out a shooting star at one point
>she nuzzles against you, sounding a bit sleepy
>"Thanks too, for not pointing out some very unladylike behavior."
>you give her a puzzled look
>she meets you with lidded eyes, suddenly very close to your face
>"You mean you didn't notice?"
>you shake your head, her purple eyes locked on yours
>she leans in, her breath warm on your cheek
>huskily, she whispers
>"I'm not wearing any underwear today."
>your brain takes a full three seconds to process the sheer absurdity of what she just said
>the two of you both burst out laughing at the same time
>it takes a long time to stop
>as you lay there trying to catch your breath, she wraps her hooves around your chest in a warm hug
>you return it happily, the two of you still giggling
>letting you go, she plants a soft kiss on one cheek
"Headed inside?"
>you ask, sad to let the moment pass
>"Yes, afraid I must if I'm going to catch any winks before work..."
"Alright. Think you'll be coming to the Mare for another drink or five tomorrow?"
>she shrugs
>"Maybe. Will you be there if I do?"
"Wouldn't miss it for the world."
>"The beer, or me?"
"Yes."
>she rolls her eyes but smiles at you, leans down and meets your lips with hers, lingering just a second.
>"It's a date."