- Jerkass Woobie:
- Gray is a playboy, yes, but seems to have genuinely loved Peach, since he drinks all the time in order to numb the pain he feels over their failed marriage.
- Magenta. Sure, she bears some responsibility for ruining Gray and Peach's relationship, but the ending of Pretentious Game 4 reveals that, despite doing a lot of good in her life, all anyone remembers about her is that she was a homewrecker.
- The Woobie:
- Blue falls in love with Magenta, but his feelings are unrequited. He finds some happiness with Peach, only to die by getting hit by a car.
- Peach marries Gray, who cheats on her with Magenta. She divorces him and falls in love with Blue, but then her new boyfriend is accidentally killed by her drunken ex-husband.
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