Woahhhh if asks are open... can I ask for Gintoki trying really hard to impress this girl he likes, but everything goes to absolute shit because this is Gintama? Totally fine if you delete! I still devour all your old stuff to fill my soul with life 🥹 Never come across anyone who writes Gintama as accurately as you bebe 😘
Sakata Gintoki Headcanons:
If Gintoki made a list of pros and cons about himself, it would probably read like this:
Pro: he has a big dick. (Big dick reading as BIG DICK, in bold, all-caps. Triple underlined.)
Con: he's a perfectionist. (Con: he's a liar.)
So, it isn't all that hard to imagine impressing you would be a Herculean task for Gintoki.
Asking Kagura for advice is like shooting yourself in the foot. Gin-chan is penniless, she says matter-of-factly. No lady wants a broke, mooching, deadbeat boyfriend. A pause to let him absorb these insults, and then, Papi brought Mama three heads, she kindly tells him like it's the secret to your heart, and that's very romantic in Yato culture apparently. Which reminds Gintoki that Kagura is from a different species just as much as her barely counting as female to begin with. Well, in human culture, he could give you as many heads as you'd want— but that's bases away and he's been swinging strikes all throughout this sad, unrequited game.
Asking Shinpachi— no, no. Now, that's a lost cause.
He tries. He does. He really tries.
He tries complimenting you. Suavely slide in a comment about how your teeth looks like it could bite into hard candy, no problem. That your hair doesn't look as dry and brittle today than it did yesterday, and oh wow, your tits look... wow. Double thumbs up.
He tries paying for your meal, to show that he can provide for you, that he's not going to be the broke, mooching, deadbeat boyfriend Kagura deemed him to be. Work a few odd jobs and have all the correct bills in his normally depleted wallet, even break a comb on his hair and get dressed to the nines in his nice, regular clothes that passed the sniff inspection when he shook it out from a pile of unwashed laundry— and it's just, while on the way to his favorite family diner he invited you to, he's passing by a pachinko parlor, with all of its flashy get-rich-quick displays and bright dinging noises from within, and that was when he's suddenly sensing it... the taste of victory. Long story short, the only thing he'll end up tasting is the strawberry parfait that you paid for.
Whatever poor progress that manages to inch forward always ends straight back to the negatives. Damn the perverted stalker and her masochistic plays she forces on him. Damn the timing and whatever deity has pitted against him when you step onto the scene to the sight of him wielding a paddle as the stalker squeals happily while tied to the wooden cross. No, this isn't— he wants to tell you, but your expression has already smoothed into a carefully blank canvas before you turn your back to him and walk away to leave him to... it. No, this isn't what it looks like, he wants to scream.
In a mood of desperation and shots deep in cheap gutter sake, he'd even wrote a poem in the dead of night, detailing the color of your eyes and all the things they reminded him of, invented a new word just to make a rhyme with your name, how the sound of your voice catches in his chest when he hears it— shit if he knew anything about pretty words, he'd never wrote anything longer than a drawn penis before— and once he was done, what he did next was ball the whole sheet up, open the nearest window, and pitch it to the stars. The lamest shit he ever did in his life will be taken to his grave.
Sometimes, because his name is Gintoki, and he is the protagonist of a septic tank for low hanging fruit comedy series called 'Gintama', sometimes the whole universe is against him.
There is a two episode-length arc the occurs, but due to the time-constraints of these headcanons and the writer's own laziness, the details of it shall not be outlined, but please know it involves an exposition, conflict, rising action, a climax (and not the good kind), falling action, some explosions and a tiny grave misunderstanding that leaves you storming from the wreckage in fury and exasperation, and Gintoki catching your wrist, spinning you around to face him. Emotions and adrenaline running high, chests heaving in exertion, and seeing your face covered in soot and sweat and your eyes huge and wet, looking damn more beautiful than you have any right to be, that's when Gintoki finally decides to put his big balls to use and confess himself to you. Opening his mouth and—
Plotfully, the wind picks up, and then suddenly a wadded ball of paper rolls to hit your feet. Both you and Gintoki look down to stare at this interruption. You bend down to pick it up and unfold the ball, startling at whatever you find, snapping your eyes up to him. "Gin, your name is on here?"
Shit! Gintoki realizes, recognizing the paper now. This is the worst possible timing! My stupid shitty poem somehow found its way to the woman it was written for. And why the fuck did I sign it!
He looks left and right, searching for a vending machine to put his head through, and when there are none, he's scrubbing his face with his hand, looking at you and the damned poem he wrote that found it's way to you, as if was meant to be there. "I wrote it." He finally grumbles. "For you. Don't be creeped out."
Your eyes scan the page from top to bottom, reading. Your eyebrows shoot up, looking up at him with wide eyes.
"This is really what you think about me?" Your trembling voice barely above a whisper.
Gintoki pauses. Then nods. "Yeah. Every word."
Your expression blanks. You turn the wrinkled paper around. Gintoki squints.
Shit! Gintoki thinks. I was so drunk I never wrote anything down, I just drew a penis!
