Aw man I’ve got sadcanons about this idea actually buckle up buddy, this also contains spoilers if y’all ain’t reading the manga, so be forewarned.
So Yagi “Scarecrow Complete Without Brain” Toshinori is probably not in the marrying mind, because he’s fully aware that his time left is entirely limited. If you can get him over the isolation he’s put himself into for what he believes to be his last few years enough for him to actually date you, I don’t think marriage is a thing he’s considering very hard, because Until Death Do Us Part is for him more like Until December Do Us Part. It’s sad, I’m sad, but Sir Nighteye was wrong about at least two things, so we’re moving forward and hopping on that Positivity and Funnies Train where the bad guys never win and All Might is always Plus Ultra. So, say one day he thinks, “oh, man, what if we were married?” He will first have a Full Blown Panic Attack thinking about it. Dawg I have panic attacks thinking about it and I’m currently single, you KNOW ya boi Shriveled Bag of Seaweed is going to have a newfound fear put into him. I do think he would propose, but also 1. He’s not one for huge gestures that might rat him or you out as being... well, him and you, and 2. He probably doesn’t know how to do it in a way that would be big and romantic anyway, also 3. He’s probably a little old fashioned that way, and wants to be the proposing party. You maybe would have had to at one point brought up the topic casually, at which point he definitely choked nearly to death on his milk, turned it into some Strawberry Milk with all the blood and coughing, and then you realized you could Never. Bring It Up. Again. But he fixates on the idea, and soon he’s awkwardly shuffling through jewelry magazines and occasionally pouring through diamond stores. He vacillates between wanting to be modest and not too showy and being the Gaudiest, Tackiest Animal Ever To Exist, so he’s either going to finally decide on a lovely and modest ring, or a huge flashy piece of shit rock that looks like you could take out someone’s eye if you punched them even slightly. There are no middle sliders here, so choose carefully on the type of ring you think would suit you best. Doesn’t matter your gender orientation, either, he doesn’t know shit about shit anyway, so whether you’re a boy, girl, combination of the two, neither, or something completely different, he’s going to get you a pretty ring. So you’re going to be at home probably when he proposes, because being in public surrounded by people while he does some sort of romantic display causes him the Anxiety, and more than likely he’s going to be Visibly Uncomfortable for the time leading up to his planned proposal. And, I mean, More Nervous than you have probably Ever Seen Him Before. You’re going to think he’s about to break up with you or tell you he’s having an affair somehow or that he has a secret child you didn’t know anything about. But he’s going to start rambling - a speech for the ages, but with no discernible plotted path or reasoning. It’s going to be a nightmare monologue, he’s going to bump his shin on your coffee table (fucking again god damnit) as he gets down on one knee, and he will not be able to make eye contact as he shakily pops open that weird little ring box and also The Big Question. He will be shaking like a leaf so bad that when you inevitably say yes (because how could you possibly say no to him??) he’s going to drop the ring three times before you have to put it on your own finger. He’ll be overjoyed, noticeably relieved, and you can start on your pathway to (temporary????) wedded bliss.
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