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In hindsight, Takao brought it on himself, when he suggested that Midorima and Akashi, go do some fun activities together, to help rebuild their friendship.
He might have still gotten out of it, if he'd been able to stop himself from teasing Shin-chan, by making all those date-like suggestions, such as... well... dramatic transportation methods. But it was just kind of... Irresistible needling that stone-like face!
... So really, he had no one but himself to blame, when he ended up being tricked into carting them both around in the rickshaw. At least they both looked like they were having fun?