Kei Ogata
The protagonist of Pure Mail. Also one of Makoto Itou's half-brothers.- Brother–Sister Incest: has two endings where he hooks up with Ai, his own half-sister.
- Dark and Troubled Past: More than most of Tomaru's sons.
- Depraved Bisexual: in addition to impregnating his sensei's underage daughter, he also raped Miki's younger brother, Taisuke.
- Hidden Eyes: In the visual novel.
- Incest Is Relative: Midori, Miki, and Rin Sekihata are all his half-nieces.
- As mentioned above, there are also two endings in which he ends up with Ai, his half-sister
- Loves My Alter Ego: The main conflict is the fact that his crush Midori is unaware that he is the one behind the internet identity A, W, whom she has a crush on.
- My God, What Have I Done?: in the OVA after raping Miki
- Not So Above It All: like his father, Kei would canonically impregnate his sensei's daughter, Rin Sekihata, while she was underage, on top of which he would molest their daughter, Korin, seven years later. And then there's what he did to Miki's younger brother...
- Sex Slave: Is this to Yumi in the OVA, who blackmailed him into it since she has proof of him hacking into the school system.
Miki Sawanaga
A main heroine of Pure Mail. She's also the older sister of Taisuke from School Days.
- Ambiguously Bi: in her route, she confesses to Kei that Midori was her first crush.
- Babies Ever After: according to the adultery chart, she has a child with Kei.
- Betty and Veronica: the tomboyish and outgoing Betty to Midori's shy and reserved Veronica and Kei's Archie.
- Incest Is Relative: hooked up with Kei and had a child. Sadly another case of incest on this page, as Miki is the daughter of one of Kei's half-brothers, Ayumu.
- Love Hurts: Poor Miki in the OVA. First, she finds out that Kei doesn't reciprocate her feelings and even gets raped by him during the fireworks festival. It's a wonder that she was still willing to see the good in him.
- Love Martyr: In the OVA, even after Kei rapes her, it's clear that she still loves him given that she was willing to forgive him (even going as far as to decide not to report it) on the condition that he treats Midori (whom she knows is his "real love") right.
- Love Triangle: With Midori to Kei. Canonically, she won.
- Passionate Sports Girl: A basketball star in her school years and a gym teacher as an adult.
- Tomboy and Girly Girl: The Tomboy to Midori's Girly Girl.
- Tomboy with a Girly Streak: tomboyish as she is, she does appreciate the school's flowerbed and can send Kei pressed flowers.
Midori Nagawa
The main heroine of Pure Mail- Betty and Veronica: the shy and reserved Veronica to Midori's outgoing and tomboyish Betty and Kei's Archie
- Dark and Troubled Past: was once a child actress whose letters to her (recognized) father were intercepted by her mother and her manager, the latter of whom answered those letters while pretending to be said father. The letters were all compiled into a sensational book, and Midori has had trust issues ever since.
- First Love: To Kei (and Miki)
- Incest Is Relative: Kei is her half-uncle.
- According to the adultery chart, she ends up having a child by Ayumu. Who happens to be her birthfather.
- Loves My Alter Ego: she has a crush on Kei's chatroom persona, A,W.
Ai Ogata
Kei's younger half-sister.- Brother–Sister Incest: has two endings dedicated to her
- Childhood Marriage Promise: in her route, it's revealed that she and Kei pinkie swore on such a promise when they were younger.
Eri Aoba
Ai's best friend.- Dark and Troubled Past: was often bullied by other students and even teachers due to her brother's delinquency and their mother's profession as a "water vendor."
Ryouka Yuuki
The representative of Kei and Midori's class.- Demotedto Extra: in the OVA.
- Rich Bitch: to Miki and Midori
- Riches to Rags: in all routes, including her own, her family goes bankrupt.
Yumi Matou
A third-year student in charge of the school's server.- Sex Slave: blackmails Kei into being one in the OVA
- The Sociopath: in the OVA, she makes it clear that she enjoys the terrified look in Kei's eyes
Rin Sekihata
A hidden heroine who's also the daughter of Kei and Midori's homeroom teacher.- Absurdly Youthful Mother: to Korin Sekihata.
- Adapted Out: of the OVA
- Dark and Troubled Past: her mother left her and her father for Tomaru Sawagoe. Her father has been harsh on her ever since.
- Incest Is Relative: Kei is her half-uncle. Not that either of them knew that...
Shin'ichi Shiba
Kei's self-proclaimed "best friend"- Adapted Out: of the OVA
- Bromantic Foil: to Kei
Hideo Aoba
Eri's older brother. As well as Yumi Matou's ex-boyfriend.- Adapted Out: of the OVA.