Blue Skies adds a few new supporting characters to the game.
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Sakurai
Sakurai is MC's homeroom teacher and also is a history teacher, known for being one of the most chill teachers in the school.
- Beware the Nice Ones: Near a certain Downer Ending of Natsuki's route, he gets pretty miffed at MC for falling behind in schoolwork, which serves to highlight how much the struggles of MC's relationship with Natsuki has interfered with the former's life.
- Cool Teacher: Sakurai is laid-back and often engages in witty banter with his students.
- Shipper on Deck: He also teases MC about his relationships and gives love advice.
Mom
MC's mom. She works abroad as a businesswoman, so she's not home often. Mom tends to give good advice to MC.
- Amazingly Embarrassing Parents: When she meets MC's girlfriend in-person, she relentlessly embarrasses MC in front of her. Also, she apparently did something super embarrassing at MC's elementary school graduation.
- Leitmotif: She has a casual piano piece as her leitmotif, and a sadder variant when MC talks to her after he gets into a fight with Yuri.
- Moment Killer: When Sayori takes MC to the park and is about to confess her depression, Mom calls at precisely the worst time.
- Parents as People: Mom tries to be there for MC, but her job makes it difficult for her to support MC as much as she'd like.
- Shipper on Deck: Mom thinks MC and Sayori are a good couple, and will be surprised if he dates someone else. If MC does end up dating Sayori, she will claim that she already knew about it and calls it "motherly intuition". Regardless, she likes to tease and embarrass MC over the phone about his crushes, and she also gives genuinely good love advice.
- When You Coming Home, Dad?: As mentioned above, her business trips prevent her from spending much time with her son.
Emi
Emi is MC's class friend. She's part of the track team and is always trying to convince people to join the track team.
- Genki Girl: Very energetic, blurts out whatever she's thinking.
- Homage: To the character of the same name from Katawa Shoujo.
- Non-Uniform Uniform: Much like Sayori, Emi keeps her blazer open. She doesn't wear the vest, either.
- Shipper on Deck: Emi tends to tease MC about his relationships and relentlessly pushes him into pursuing his crush.
- Shout-Out: She mentions her boyfriend once being in the hospital for heart-related problems.
Shiori
Shiori is MC's homeroom class rep. She is one of Monika's friends.
- Non-Uniform Uniform: She once came from a strict school that required students to wear uniforms even outside of school. To compensate, she now heavily modifies her uniform. She keeps her blazer open, doesn't wear the vest and wears a tie instead of a ribbon.
- Precious Puppy: Shiori has a fluffy dog named Mochi.
