I wish I had time to write this in detail, and maybe I will one day.
But my favorite headcanon for Raph and his s/o is that when he really decides that he is wants to ask them to marry him.
He freaks out.
All of his self loathing and doubt about being a giant mutant turtle that lives in a sewer of all things come flooding back and for a week he runs off and hides.
His S/O calls him a few times, then his brother and his s/o, but it really hit him hard when he hears the panicked messages and sobbing that it’s never been about him being a mutant turtle, and that his s/o truly does care and is currently in pain and sacred out of their mind. So he calls them and they talk and he genuinely apologizes.
He’s run off but never without a reason that the others know about, that someone knows about.
He spends the night at their house that night and the next day he gets to work. He needs a ring.
He’s going to do this shit.
But it can’t be any ring. He refuses to steal it, and he absolutely refuses to give them one he found in the sewers. He thought about making one, but the love of his life deserves everything, so he’s going to get those damn jewels.
He tries to think of ways to get the money together, and he can’t so he goes to Donnie, and though he won’t tell Donatello what it’s for they hatch a plan. Too many months later and a LOT of carving, knitting, and forging he’s got a considerable sum. Even Donatello is a little surprised at how much Raph hoarded.
Raph spends every last cent in one go on a silver ring with a large ruby set in the center of a diamond lotus. When April hands it to him a week later, he withdraws again, spending a lot of time staring at the tiny box, flipping the lid open and shut. He’s nervous again. Terrified really. The ring is one thing but he can’t even offer a proper ceremony, a proper home.
Mikey finds the box. The whole family immediately knows. Donnie and Splinetr smile. Mikey says that if Raph chickens out, he will ask instead.
Leo puts a hand on his shoulder and tells him that married or not he still has a job to do.
They laugh together.
Raph pops the question a week later. It’s risky being out on street level, New York never sleeps. But it’s Christmas time again, and the city was ablaze with lights, people and gorgeous displays. It was hard not to resist the pull of it all.
It’s too cold for world famous banana pudding, but Raph, covered head to toe in coats and scarves agrees to wait nearby, his heart beating out of control as he checks his pockets every five seconds.
They use the rooftops to get to Central Park, he doesn’t set them down till they get to his set destination, Belvedere Castle. Well past visiting hours, he sneaks up to the highest observation floor. His hat comes off and his scarf gets pulled down. Nuzzling their shoulder as they look out over the lake, Raph can’t decide why he even thought his city was beautiful without them in it. He wanted to wait till after they ate, but he couldn’t. He was too nervous. He kisses their cheek as he pulls away….
..and drops to one knee.
The pudding falls. Raph catches it with his other hand out of reflex.
But with both hands full, he can’t catch the love of his life; the force of the hug sends them all sprawling back into the snow.
A few heated kisses later, he remembers the ring.