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Shouto and his adoptive sisters, part 1

I headcanon that Todoroki is especially protective of Uraraka (e.g. in Movie 1 he intentionally placed himself right in front of her) and Asui, because they remind him of his sister, who is both cheerful and caring, and to whom he couldn’t be close to in the past. Despite being the youngest Todoroki sibling, and the one who received the brunt of their father’s abuse, I think Shouto might still feel partly responsible for the distance between him and his siblings.

It seems like Todoroki joined Deku & co for lunch regularly, right after the back-alley trio returned from Hosu. I headcanon - especially since I've watched their background shenanigans in the BNHA stage plays (the plays are hilarious, go look them up on yt!) - that Uraraka started to uraraka-handle Todoroki around the place, just like she has been doing with Deku and Iida since the start.

And no, their friendship doesn’t consist of Todoroki buying her expensive shit with his father’s credit card. Todoroki was someone who rejected his father’s instructions for years, even though it would have benefitted his hero training greatly (makes 100 % sense from the emotional angle, and 0 % sense from a sheer utilitarian angle). I headcanon that he also refuses to ask his father for money for anything. Fuyumi took care of that, otherwise Todoroki might have just walked around in clothes that he's grown out of, just because he didn't want to ask the old man for anything.

I also don’t think that Uraraka would accept huge amounts of money/monetary gifts from her friends, no matter her own financial circumstances. Even - or rather especially - if she'd thought that Todoroki's spending his father's money on her to piss of the latter. I think Uraraka would have an outlook like, “Don’t do things mainly to oppose someone. Do things for yourself!” which redirects Todoroki’s actions away from his father but turns his focus towards himself.

Uraraka would grab Todoroki and their friends, and they would go to the nearest playground. Each of them teaches Todoroki how to play their favourite (and entirely free of costs) childhood games. The games he wasn’t allowed to play, when he was younger.

He will catch up on them now. Together with his friends.

...

In my mind, this was canon:

For sure, Uraraka's first impression of Todoroki is of him being an awkward oddball... which I headcanon is one of the reasons why she went out of her way to befriend him.

Shouto and his adoptive sisters, part 2

Would have loved to see an actual team-up between these two: The guy who thought his quirk works best without teammates around him, and the girl known for being one of the most versatile battle comrades you can have.

Asui is the older sister to two younger siblings. I headcanon that she talks to Todoroki like how she talks to them: Encouragingly and patiently, without any condescencion.

They got closer after Asui cried in front of him and the other kids, who sneaked away to Kamino. Todoroki was reeeally sleepy, but he still felt bad about having partly caused her distress, so he tried to talk to her more afterwards.

When the weather turns cold, Todoroki and Asui often end up sitting close to each other: First on the school bus, then anywhere else. Todoroki gets some comfort out of seeing how his fire side, which he had rejected for so long, can be helpful to others even outside of combat - be it to keep Dark Shadow obedient to Tokoyami, or to keep Asui from involuntary hibernation.

Headcanon: Todoroki intentionally chose the spot in front of Asui and Uraraka. He wanted Deku and Iida to join them but before they could, Aoyama and the other girls placed themselves around 1-A's pretty boy.

I saw a fan comic once, in which Asui brought Todoroki a cup of tea and he accidently refers to her as “nee-san”.  I headcanon that this has happened more than once. Todoroki’s cheeks turned rosy the first couple of times. Then Asui asked that he call her “Tsu-chan”, and he felt even more embarrassed by that.  

As such, Asui remains “Asui” when they are with others. She doesn't correct him, because when she’s alone with Todoroki-chan, she gets to hear “Tsu-nee-san.” Todoroki ends up calling her that nonchalantly. They also ignor that he's actually a month older than her. Considering how he doesn’t use honorifics with any of his other classmates, Asui feels rather special.

Todoroki really does emit youngest child vibes sometimes.

It seems like, barring Deku and Bakugou, most of Todoroki’s classmates didn't know anything about his family drama, until Dabi broadcasted it to the whole nation.

For example, I’m don't think Iida ever picked up on anything prior to Dabi’s dance. He's probably Todoroki’s closest friend (alongside Deku), and he cares a lot. But Iida also tends to be blind to emotional undercurrents. In one of the light novels, he accidentally pisses Todoroki off by telling him off for how he refers to his father. When he visited Todoroki in his room on Troy, he also made a well-meaning but misplaced comparison between their families.

However, a few of them did take notice of Todoroki’s complicated family life, e.g. Kirishima (Todoroki didn't hide much in BNHA's supplementary works). I headcanon that Uraraka and Asui were also among those, who at least picked up on the fact that Todoroki had grown up in a very strict environment. Thus, they tried extra hard to include him in their conversations and activities. This might have contributed to Todoroki warming up to the rest of the class much faster than he might have done otherwise.