YMMV: don't take it personally babe, it just ain't your story
- Alternate Character Interpretation: Rook — earnest teacher in over his head or horrible teacher and sadsack creep? Arianna — calculating Fille Fatale, or hopeless naive romantic who thinks she's not? Kendall — the most awesome person ever or the most annoying person ever? Nolan — put-upon boyfriend, or cocky douchebag? And finally, Taylor — manipulative bitchy popular bully with no regard for anyone's feelings, or troubled teen who's bad at people skills and doesn't understand why she's losing friends? All of these are supported by one path or another.
- Headscratchers: It's plausible enough that John only has one class of eight students considering it is a ridiculously expensive private school. But where are the other teachers? John never interacts with them and the kids never talk about their other classes, or for that matter to or about other students. Frankly, it is extremely unsettling.
- Internet Backdraft: Quite a few people hate the Rook/Arianne plot. So much so that when the game was given a Let's Play on the Something Awful forums, the user had to assure everyone "I'm not doing that subplot."
- 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 C Gs 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.