Some people say that Daddy Dearest isn't really that evil, or is doing everything to stop you. He's just not willing to let his daughter go, and all he's trying to do was to test your skills before he could have faith in you, and allow his daughter to be on your side. The same could also be said for Mommy Mearest. This was probably jossed in later updates: Week 5 has them holding the mall's Santa Claus at gunpoint, and Week 6 reveals that Daddy Dearest apparently was the one who trapped Spirit in the dating sim forever, and is implied to have done similar things to other people. Word of God even said that the parents attempted multiple times to kill Boyfriend. Even that is contestable though. Did Daddy Dearest trap those people because he's evil, or was Spirit genuinely such an asshole that he took it upon himself to seal him away? Was Spirit even that hostile before he was trapped in the game? If many were trying to use or bring harm onto his daughter, does that explain why Daddy Dearest doesn't trust Boyfriend even several weeks into his and his daughter's relationship? For that matter, could it be that Daddy Dearest is evil, but he doesn't want other evil people messing with his beloved daughter?
The Monster is subjected to this in spite of limited context to his involvement. Is he a vicious monster out for a gourmet serving of flesh, or just some creep with a twisted sense of humor and singing style? For someone so seemingly adamant on eating the protagonists, he seems content with singing some catchy tunes and then letting them go on their way. His danger is alluded to when the mall evacuates when he reveals himself and the place is lousy with blood and guts, but that’d leave it to a toss up whether that was all a bluff or he sincerely got humiliated enough from being bested in his song to let Boyfriend escape.
Regardless of the ambiguity of how evil or not Girlfriend's parents are, many have questioned what's actually going on during Mommy Mearest's week. While it's easy to see her as just as much of an overprotective parent as Daddy Dearest, a combination of the general rhythm of her songs along with Mommy Mearest and Boyfriend frequently performing outright duets makes it seem more like she's actually just having some fun singing alongside Boyfriend. Building off that interpretation, quite a few players take their battle as actually being about Mommy Mearest fully supporting Boyfriend and Girlfriend getting together, with the competition instead being her testing how far Boyfriend's willing to and capable of going for the sake of her daughter. This is somewhat jossed with Week 6's update, which gave each week an official name. Hers, Week 4's, is titled "Mommy Must Murder", which doesn't indicate friendly competition.
In Week 6, the female student NPCs in the background look smitten with Senpai, but when he starts getting angry by the second song, their heart-eyed expressions turn into ones of absolute shock. Are they taken aback by Boyfriend being able to keep up with Senpai's singing specifically, or are they reacting to Senpai's complete change in demeanor and attitude?
In much the same vein, Spirit himself. We know more or less "why" he was trapped in the game, but only on a surface level. Was he merely a past suitor who got on the wrong side of Girlfriend's father, or was he secretly a Jerkass who was dealt with swiftly to get him out of the picture? Seeing as how he infiltrated every aspect of the game's code after being trapped there, it could explain Senpai's rather sudden rudeness after Boyfriend proves himself in Round One of Week 6. However, that idea is jossed once it was confirmed that Senpai's behavior was confirmed to be his true nature. He's a sore loser and is only used to being loved, to never lose against anyone in his game.
During Week 7, why did Pico decide to save Boyfriend and Girlfriend out of nowhere? Was it because he was just bored? Was he hired once again by Daddy Dearest to save his daughter? Or was he doing it out of simply not wanting to see the couple die? Turns out to have been because he was contracted to confirm Boyfriend's death by Daddy Dearest and he merely could not allow Girlfriend to die.
Word of God states that like Boyfriend, the reason Girlfriend is unfazed by the constant life-threatening situations the two find themselves in is because she's simply too dumb to realize that they're in danger. However, Week 7 casts doubt on this considering that she was seconds away from using her demonic powers against Tankman after he orders his men to shoot her, only stopping due to Pico's sudden arrival. This begs the question: Is she really oblivious to how much danger they're in? Or is she just so confident in her ability to handle any genuine threats that she doesn't bother caring?
