Considering that Crispin somehow obtained Nicole's phone number, and sent her an unsolicited dick pic after meeting her just once, some players have theorized that he's not really as nice, or as oblivious as he acts, and is really just using weaponized incompetence to hide the fact that he's just as manipulative, and predatory as everyone else, and that him constantly "accidentally" running into her at places (even at places other than school) isn't in fact random, but is the result of him stalking her.
Jeffery can either be seen as a run-of-the-mill Hormone-Addled Teenager with No Social Skills or a future pedophile just waiting to happen depending on how his habit of oversharing his fetishes gets interpreted. Most notable is Nicole bringing up how his type talk about lowering the age of consent during one of their first potential interactions. Being that it's Nicole who brings this up, the reliability is suspect, but it should be noted that Jeffery himself doesn't object or try to correct her on it.
Some fans posit that Nicole isn't actually a pure sociopath like she describes herself as but rather just woefully out of touch with her own emotions. While she does do a lot of terrible things to other people with only the slightest bit of provocation, she's shown to be capable of forming relationships with other people like Jecka and Emily with no strings attached, never intentionally humiliating or harming either of them even when they do snipe at her. During the route where Nicole temporarily ruins her friendship with Jecka, Nicole actually goes out of her way to help Jecka out at the expense of having to regularly see the pedophilic counselor. While she could have just been doing that out of pragmatism so she wouldn't be seen as a loner, the extent she was willing to go to feels at odds with someone who by all accounts shouldn't care at all about her attachments. Nicole at times reads less like an actual sociopath and more like someone who wants to be one to not have to deal with the potential pain that could come with actually caring about someone else.
One story path with Kylar can have him jump off a building to impress Nicole. When Nicole comes home after the incident she finds out that Kylar died in the hospital from the sustained injuries. However, Nicole is not affected at all and is more upset that she didn't take more of Kylar's drug supply.
Twice in Re-Up
If skipping in the mall, Nicole can end up getting shot by the mall cop. Two weeks later, she shows up in school again with very little emotional baggage about the incident. Jecka on the other hand...
If skipping at home, Nicole abusing her mom's prescription with Jecka leads to her mother dying. However, once she's back at school, she is the same as ever and even admits to Jecka that she didn't cry over her mom's death at all, which Jecka finds disturbing.
Watching the Coach and the Councelor get dragged away by the police for their child-molesting ways will bring a smile to most people.
Despite being a Jerkass Woobie, some of the bad endings where Nicole is arrested, institutionalized or otherwise reaches the end of her Karma Houdini Warranty can also be quite cathartic.
The two ways Nicole can respond to Jeffery's request to sign his year book after he nearly distributed porn of her as revenge (either writing how he'll likely end up in prison in the future for dating a teenager or just flatly refusing) is one of the very few occasions where her bullying him actually comes across as justified.
Crosses the Line Twice: The game pretty much obliterates the line in its opening cutscene and just keeps on going from there. You will laugh and you will feel pretty bad about it afterwards.
Nicole being a sociopath is outright stated, but it's heavily implied that she's also suffering from depression. She consciously engages in self-destructive activities, struggles to find reasons to even get up in the morning, can't find the motivation to do much of anything but space out unless motivated by raw spite, rarely reacts strongly to outright threats on her life, and admits that she doesn't plan to live past 30. Being depressed could also possibly explain why Nicole took great offense to Ari "stealing" her depression excuse during one route in the Re-Up
Jeffery's habit of oversharing and constantly talking about his special interests to people without realizing that they're clearly not interested, along with his general lack of social skills, can make him come across as being on the Autism spectrum.
Since Emily takes Seroquel to keep her "mood in check", many people speculate that she has bipolar disorder and schizophrenia. During her route, Emily decides to go off her medication resulting in her becoming a Mood-Swingerand Hearing Voices.
Draco in Leather Pants: Nicole gets a lot of this by the fanbase, largely thanks to her having a sympathetic background and Freudian Excuse for how she is the way she is. A lot of people seem to think her outing the school's faculty as sexual predators is an example of her having an actual moral principle against it, despite other routes showing how she will willingly have sex with these same predators if it personally benefits her, meaning it's less a case of Everyone Has Standards and more a case of her just knowing the most effective way to screw over people.
Many people like Crispin for his endearingly airheaded personality, and for the fact he's the only genuinely nice person in the game. That is, if he's not just faking it all.
Emily is also well liked for her snappy comebacks, fun route, cute design, and for telling off Nicole's mother who had taken a massive level in jerkass in the Re-up.
Ari manage to gain quite a bit of popularity after getting her own route in Re-Up due to her sympathetic Coming-Out Story and being A Lighter Shade of Grey among Nicole's potential romantic options. During a twitter poll on which characters fans wanted to see in the upcoming anime, Ari overwhelmingly got the most votes.
Mall Cop is beloved for his explosive Large Ham declarations of wanting to kill his wife and anyone who breaks the law, being one of the few adult males who isn't a pedophile, and his amazing voice acting (courtesy of Josh Tomar). Many players wish he could show up beyond some early scenes.
Despite the fact people in-game hate him so much that that they outright celebrate his death, Kylar is loved by the fanbase for being such an over-the-top stereotypical, idiotic bigot that nobody in-universe or out can take seriously.
Even Better Sequel: Or Interquel in this case. Re-Up is seen as a welcomed improvement of the original game due to having more memorable jokes and scenarios while giving a lot of focus on the first game's Ensemble Dark Horses like Emily and Ari.
Fan-Preferred Couple: Due to their great chemistry, the game's most popular ship is Nicole/Jecka ("Jeckole"), despite Jecka not being a romantic option for Nicole, even though there is plenty of subtext that implies that Nicole is attracted to Jecka. However, due to the "rejection sim" nature of the game, this might have helped made the ship so popular since all of Nicole's optional relationships tend to end as a dysfunctional mess at best or have fatal consequences at worst. Hilariously, in-story Jecka refuses to have a intimate relationship with Nicole because she (rightfully) assumes that Nicole will be an abusive partner.
Genius Bonus: In the LA ending in Re-up, Nicole says during her narration that the payout she got from her lawsuit against the school was "so hot" before mentioning she's met another Nicole in LA who's famous. The Nicole she's referring to is Nicole Richie, Lionel Richie's adopted daughter who was famous during the game's 2007-08 timeframe for frequently club hopping around LA with Paris Hilton, with Richie coining the phrase "That's hot" during the time period. Evidentially the two Nicoles met through their shared taste for expensive narcotics. By the time of game's release, Nicole Richie had long since faded into pop culture obscurity and only players who themselves were teenagers in 2007-08 would've understood the reference.
Hilarious in Hindsight: Most likely intentional due to the time period in which the game take place since nobody could have possibly predicted it back then, but the fact that Ms. Ames has a special dislike towards Kanye West of all rappers when he is likely the sort of guy who would share many of her racist views should earn some chuckles out of some people.
It Was His Sled: Part of what makes the White Nationalist routes so hilarious and memorable is the shock value - the game teaches the player to just assume Mr. White is another pedophile, only to go in a completely different direction. As the scene and the series has gotten more popular, however, it's become increasingly difficult to hide the twist from people just walking into the franchise.
Nicole is by no means a good person, with her regularly insulting (and sometimes bullying) her classmates, doing criminal activities like selling or taking drugs and having no empathy in general. However, considering how most of the male teachers at her school are willing to date or hit on her, her father committing suicide, her mother not seeming to care much about her, her male classmates acting like creeps towards her, and the fact that she's genuinely suicidal... It's not hard to feel bad for her.
Jeffrey is annoying, entitled, and sometimes downright creepy, but he's also far less of a terrible person than Nicole is and it's genuinely sad to see her and Emily sabotage his relationship with Karen just because they didn't want him to be happy. The phone messages implied to come from him also reveal that he is a lot more affected by being alone than it initially appears. By all accounts, he's just a kid with No Social Skills surrounded by peers who aren't forgiving of that fact, which does make him incredibly pitiable even when he does nothing to correct the worst parts of his behavior.
Jerks Are Worse Than Villains: Surprisingly averted. The only reason it's even remotely possible to root for Nicole is because of how many people she gets involved with who are leagues worse than her and the fact that her cynical worldview actually seems entirely correct in the world the game takes place in.
Despite the story being a Deconstructive Parody of dating sims where characters trying to form a relationship with the main heroine tends to end in disaster, the fan base constantly ships Nicole primarily with her female classmates such as Jecka, Emily, Ari and Megan.
Ari herself gets shipped with most of her female classmates, even Nicole despite Nicole abusing her so badly in their relationship route that it traumatized Ari from ever dating another girl again.
LGBT Fanbase: A surprisingly large fan base given the humorously over-the-top offensive dialogue due to the Deliberate Values Dissonance of the late 2000s settings. While Re-Up does play up the Les Yay and introduces a few Gay Option, those routes are suppose to be deconstructions as they show that Nicole's female relationships are just as destructive as her potential male relationships. Re-Up is even given the nickname of "Toxic Yuri Simulator" in some circles. However, a lot fan still love the extremely flawed and sometimes even relatable relationships that the characters have with each other. Noticeably, the games' most popular ships are primarily femslash, fueled by all of the game's Ho Yay and outright Ambiguously Gay/Bi moments revolving almost entirely around the female cast.
"Bitch, please give me a fry!"explanationA quote from Nicole in animated short after Emily wanted a polite request after Nicole initial "Bitch, give me a fry!"
"Are you threatening me in Skechers?"explanationA quote from Nicole in Re-Up while she was bullying Jeffery as a ploy to get herself in trouble with the Counselor.
"You wanna be sexed-up abusive lesbians?" explanation Another quote from Nicole in Re-Up when she asks Jecka if she is interested in being Friends with Benefits.
Memetic Psychopath: Some fans have taken the theory that Crispin is just faking his brainless nice guy persona, and spun it into believing he's just as bad Nicole, but he's just too lazy to act upon it, and/or just prefers to keep up the facade because he finds it easier to get what he wants by using it.
One-Scene Wonder: In Re-Up, the mall cop only shows up in one part and manages to steals the show with the over-the-top police brutality for shoplifting and Large Ham when his calm demeanor goes to Suddenly Shouting about how much he wants to kill his wife, cementing himself as one of the most memorable moment of the Re-Up run.
Realism-Induced Horror: For as much as pedophilia is Played for Laughs in the game, the idea of a school being populated by sexual predators who are allowed to get away with preying on teenage girls is a nightmarish scenario.
Ships That Pass in the Night: Ari is often paired with Karen in fanfiction usually coming off of the heels of Ari breaking up with Nicole despite them sharing no scenes together, likely because Karen is the least dysfunctional girl in the entire cast.
Signature Scene: If there's one part of the series that's well-known to people even outside the series' fandom, it's the scene of Nicole going to school and finding out that ninety-five percent of the entire school, including Jecka and even the teachers, have been indoctrinated into Mr. White's white nationalist cult. It both perfectly exemplifies the dark subject matter of the series and demonstrates how most of that subject matter is played for comedy.Even the introduction to the Re-Up takes special care to mention Mr. White's status as a white nationalist.
They Wasted a Perfectly Good Character: Most fans agree that Nicole's mom and brother are pretty underdeveloped for being the main character's closest family members. They don't even get names!
Unintentionally Sympathetic: Jeffery is meant to be a wholly unsympathetic creep like everyone else, but he's far less genuinely evil than a lot of the other characters in the game and much of the bad stuff that happens to Nicole is done in retaliation for her bullying him. Him actually being able to have a relationship with Karen only for that to be immediately sabotaged by Nicole and Emily was also completely unwarranted.
Unpopular Popular Character: In-universe, Kylar is an obnoxious Jerk Jockwho is mourned by no one after he kills himself in one route. Out of universe, he's one of the most well-liked characters thanks to him taking his stereotype so far and being so blatantly politically incorrect that everything he says loops back around to being hilarious.
on which characters fans wanted to see in the upcoming anime, Ari overwhelmingly got the most votes.