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Heyo! Just finished Toshiyuki's route, also got the happy ending, it was also bittersweet for the same reasons lol, but Shiba is still my favorite. Anywho, I'm planning on moving onto Toru's route! I've heard that you have to lose the seiyuu award to get his best ending. Is that true?

No, you need to win too. For his route, you need to win Seiyuu Award to unlock both his bad ending and best ending. It branches out at the end (I think it is a pretty obvious branch) 

Thank you! Thankfully I haven't started it yet.