- Alternate Character Interpretation works for almost every character, as both interpretations are supported, based on the chosen dialogue options.
- Rook, is he an earnest man, who wants to do well as a teacher, but is in over his head after switching his job becase of a midlife crisis? Or is he just a creep to begin with?
- Arianna, a poor misguided, but hopelessly romantic girl who honestly doesn't see how her behavior can be seen as a Fille Fatale? Or is she a Fille Fatale and is fully aware of it?
- Kendall, an awesome person who doesn't let herself get trolled, only to troll people back? Or obnoxious, because of those exact reasons?
- Nolan. Is he a put-upon boyfriend, dealing with his recently-discovered bisexuality? Or honestly a friendless douchebag, who is using Akira as means of having a friend by his side?
- Taylor. Manipulative bitch who cares about no-one's feelings but her own and feels no remorse for her actions? Or a simple, misunderstood teen who honestly doesn't understand how hurtful her actions are or why she's losing her friends?
- Jerkass Woobie: Taylor considers herself one. Her classmate's opinions on whether The Woobie part is valid vary. John's opinion depends on the player's dialogue choices while confronting her.
- Narm: The CGs aren't very good, and the fact that the style they're rendered in is so different from the usual style just makes it all the more jarring.
- Nightmare Fuel: The messages from the Shinigami are just creepy. Really creepy.
- The fact that the Shinigami will have the same last name as your character from Digital: A Love Story. If you played the second,... well first, and then play this it can scare the crap out of you as a character has the same name as you or your pen name.
- Squick: If you decide to have a romantic relationship at the start... it can be very squicky especially since the first CG is of the two of them making-out in the rain. The most you're gonna see is tits though.
- Unintentionally Unsympathetic: A common criticism of this game is that the ending can make most of the cast this. It's revealed Isabella didn't actually end her life, but actually moved away. The entire cast decided to play a prank on Rook to convince him that she died so that he'd "lighten up." Thing is, convincing someone that one of their students committed suicide, then terrorizing them with emails from an unknown person blaming them for the student's death, goes beyond pranking. This is especially true when you remember a plot point of one of Akira's mothers being upset that her son was being cyberbullied... and she was in on said prank.
- Values Dissonance: In-Universe, Rook's reaction to the revelation that the students and their parents know that the school is monitoring the students' social network AmieConnect and they don't seem to care. Emphasized more, when Rook talks about 'invading privacy' and similar... and his students have no idea what the word 'privacy' even means anymore.
- WTH, Costuming Department?: Akira dons a neon-green, longsleeved shirt underneath his schooluniform one. And a neon-pink t-shirt at other times. Seriously, Akira. What?
YMMV / don't take it personally babe, it just ain't your story