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So, Auntie Martha (grandmother to Alice), is gonna probably be cast in the motherly role more often than not, but this is a great opportunity for her to like... give advice to a young cougar-chaser??? Explain how women of a certain age prefer to be treated by young men?? His canonical, and supremely stupid, idea of making clothes with HER FACE ON THEM might be something he bemoans to Auntie Martha, because she's quite willing to feed him biscuits and lend a listening ear. And she really surprises him, (and the readers hohoho), by letting him run out of steam, and then going on a FRIGHTENINGLY WISE description-exposition scene, with Ritter's jaw falling further and further to the table as she talks, with just as much of her usual balance of lightness and severity, about how to woo an older woman.
She'd have lines like "You're not my type, dear, but I /do/ have the ear of the woman you're after, and I can tell you for /certain/ that she's the type to get into her cups... Rarely, and only for occasions of great import, but I can /also/ tell you that her beloved eldest daughter is having a wedding soon, and /that/ would certainly count for her yearly 'let her hair down' situation... And her younger son is perhaps a little miffed about the lavish ceremony that she's assured him that HE won't get unless he marries rich, so he WOULD probably be willing to let you spike the punch if you promise to make the night interesting and really embarrass the tailoress... Not his sister, the bride, he's quite loyal to HER after having to live most of his young life with HER as his mother figure instead of YipYip herself - the demands of her profession and all that...." That kinda thing.
And he tries to babble that he isn't interested in Madame YipYip ROMANTICALLY, and she pauses only for a moment before shaking her head and insisting, "Now, now, dear, let's not be precious about our true intentions - after all! Evermore is the land of DREAMS, and you won't get anywhere NEAR what you want without being honest about it!"
"N-No! ...No. I really, truly, had NOT had that as my intention, milady..." His humiliated looking face, unable to meet her eyes, even the tips of his ears sagging, convince Auntie Martha that he really DOES think that he's not after YipYip romantically.... at least for now.
"Ahh, I /see/, dear..." she putters for a while, and returns to the table, and pats the side of his cheek with slightly more force than he felt was warranted. It felt a bit like a wake-up slap. "Well, you'll have your chance, if you choose to take it. Up to you what you want to SAY once you have her full attention, after all!"
Soooo he DOES go thru the whole shebang, and eventually gets down on one knee, about to open his mouth and pull the stockings down her thigh with his front teeth... and while he sees his life flash before his eyes, he makes his choice, and declares with a hand on his heart that he wants to be her apprentice.
Her eyes go slightly out of focus and the inebriated confident smarmy grin she's been wearing for AT LEAST the past hour slightly fades. "My... what?"
He stands in a rush and grabs both her hands in his - thankfully neither at the moment contained any alcohol or it WOULD have spilled - and earnestly explains his dreams of being taught by her, and she starts shaking her head and her brow gets more and more furrowed... It seems his plea is falling on ears deafened by the pounding of a hangover's headache...
So when other, larger, dogfolk men come to prise his grip off of her, he relents, and sits in the corner for most of the party before the son, with whom he had collaborated earlier to spike the punch, comes by and pats him consoling on the shoulder.
"Didn't quite work out, huh?" Ritter shakes his head miserably. The son nods. "Well. Certainly could have gone worse. And hey - there's always next year." Ritter groans and drops his head into his hands. The son squeezes his shoulder with an edge of authority that Ritter startles at. "If there's nothing more you want here, perhaps it's time to go home, Ritter." The wide eyes his suggestion receives make the son drop his hand from the weak-framed tailor's shoulder. "Not that that's an /order/ or anything, just..." He shrugs, and tries to smile to smooth things over. "Perhaps things will be looking up in the morning, yeah?"
Ritter nods miserably, knowing that son was indeed, infuriatingly, correct, and leveraged himself up off the chair, stumbling not from alcohol intake, but stiffness of muscle from sitting still in the chair for so long - nothing at all like his well-padded workbench seat.
The son reaches out to steady him, but Ritter shoves him off, giving half-hearted words of thanks and 'we make a good team' sort of expressions that neither of them fully believe (see, we COULD form a gay-ship here, but I reeeally don't think they're right for each other in this AU. Ritter is JUST NOW having the crisis of self about whether he wants to fuck his elder female co-worker-senpai-mentor, and he doesn't have room for a gay revelation on top of that right now lol.)
YipYip's younger son was more right than he realized, Ritter discovered, when the next morning, head just as sore as he expected it to be, he discovered a hand-delivered letter in his post box, purportedly from YipYip herself - she wants to meet with him in 2 days on the Outfitters third floor! At an early morning hour commensurate with beginning a tailor's workday!? He can scarcely believe his luck, and brings the letter to Auntie Martha - who either barely drank or holds her liquor better than any sky pirate he's ever seen (simple, she has a Higgledy to purify it back to water with a spell, since she wants to keep her health in her old age) - who confirms it IS YipYip's handwriting and therefore probably genuine.
So, he can truly look forward to the start of a professional relationship! And it only took completely eviscerating his dignity to do it! A small price to pay, he thinks to himself. Not like he had much to start with!