Cliché Storm: It's pretty much just a typical Shane Dawson skit made into a full-length teen romcom. There isn't really much to it beyond that.
Critical Dissonance: Every critic who reviewed this movie despised it, one of them going so far as to say it would only be enjoyed by "date-rapists, racists and sociopaths". Nonetheless, viewers overwhelmingly voted for this movie to win the competition with Hollidaysburg, leading many observers to loudly complain that having a YouTube star competing against a relative unknown was effectively rigging the competition in the first place.
Crosses the Line Twice: The "watermelon scene" has been said by viewers to be the best part in the movie.
Harsher in Hindsight: The whole thing looks really bad in hindsight, and looked bad at the time — hence Shane pretty quickly trying to bury it and forget about it. But one particular thing people have pointed out after his image revamp is that his collaboration with blind YouTuber Molly Burke in 2018 feels really gross considering how many offensive jokes about Marissa's blindness there are in this movie, which at the time he hadn't acknowledged or apologized for.
More Popular Spin-Off: Thanks to Shane promoting this movie directly on his own channel, a lot more people saw it than saw the Reality Show competition it came from, The Chair (2014), or the other movie from that competition, Hollidaysburg. Even some of the most viral scathing reviews it has now don't seem to be aware that The Chair existed, and struggle with the mystery of how Shane got the funding to make it.
Dawson seems very frustrated by how the simple fact that his movie contains a scene of a homeless man eating his own feces overwhelms anything else anyone might have to say about their reaction to it, and that this was true even before the movie was made — and yet this didn't persuade him to take it out.
On a meta level, almost nobody talks about this movie just as a movie without talking about the context that it beat the much-better reviewed film Hollidaysburg in the Reality Show contest The Chair that it came from. It's only discussed now, as of 2020, in the context of charting Shane Dawson's overall downfall as a social media influencer. (For fans of Cherami Leigh, it's slightly unfortunate that this movie is the only time she's ever had an on-camera lead role in a feature film.)
Tori is played by Cherami Leigh, who is a well-known anime and video game voice actress. Quite a few people wonder exactly how Dawson managed to convince her to sign on.
People on The Chair (2014) repeatedly point out what a bizarre idea it is for Shane to cast himself as Scott, who's supposed to be a former Big Man on Campus and a heartthrob, which is almost exactly the opposite of Shane's type.
Slow-Paced Beginning: Shane Dawson received repeated feedback during The Chair that Not Cool suffered badly from this, and refused to change the script in the face of criticism. Notably, the movie goes on for 27 minutes before Tori and Scott have their Meet Cute and we get any indication that the movie is a love story between the two of them.
Squick: The movie has a lot of scatological humor, and some can be really disgusting, like the hobo eating his own excrement or Tori's mom sharting her pants.
They Wasted a Perfectly Good Plot: One noticeable missed opportunity is how Scott and Janie barely have any relationship with each other — something that gets lampshaded in the final act with Scott apologizing for how he's spent his whole life ignoring Janie, sure, but still comes off as a cop-out. You'd think Scott would have some kind of opinion over the fact that Joel is resorting to desperate measures to get with his little sister, but the issue never comes up, even with Tori being Joel's confidante. (It's pretty obvious that the original script this is based on had Scott as an only child and had no direct relationship between him and Janie.)
Took the Bad Film Seriously: The postmortem of The Chair had a lot of people praising Cherami Leigh and Michelle Veintimilla for giving quality performances despite the awful script and Shane's insufferable behavior. (Cherami Leigh, for her part, actually doesn't seem to share the haters' opinion of the film, and continued to make videos with Shane and hang out with him socially afterward.)
Unintentionally Unsympathetic: We're supposed to see Scott and Tori as likable because of the crazy cast of characters they're surrounded by. It doesn't work, possibly because the movie is so offensive it's impossible to turn off your awareness that Scott is played by the guy who created it. Tori, meanwhile, is such a one-note Deadpan SnarkerDariaExpy without actually being funny she's actually harder to like than the people she's making fun of.
The Woobie: Scott. It's really hard not to see him as an extension of Shane Dawson's frequently expressed Real Life self-pity.
in 2018 feels really gross considering how many offensive jokes about Marissa's blindness there are in this movie, which at the time he hadn't acknowledged or apologized for.