Let's be honest: rom-coms frequently celebrate really questionable values and champion behavior that would land you a restraining order in real life. If this movie had had a little bit more self-awareness, it could have been a pretty good parody of the genre, but it takes itself way too seriously for that.
It starts out by stretching the "lovable loser" trope way past the breaking point. Our "hero", Nate, had a crush on a girl named Cristabel in the first grade, then his family moved across the country and he never saw her again. Now an "adult" (in years anyway), he's never gotten over this. He can't stay in a relationship, or even hold a job, because he can't get Cristabel off his mind. Rather than see a therapist, he decides he has seek her out. Since Google doesn't exist in this universe, he hops in his car (which definitely couldn't have made the trip) and drives across the country to find his first grade friend, Arno. It turns out Arno has also been obsessed with Cristabel since the first grade (what are the odds?). In fact, he's been stalking her his entire life, and has compiled a full dossier with the help of his mother, with whom he lives and has a very creepy relationship. Like Nate, he appears not to have a job. In spite of his lifelong obsession, he seems to have no personal interest in Cristabel, and has apparently just been waiting around for Nate to return so he can help him win her over.
He re-introduces himself to Cristabel, the eponymous "hottie", by tackling her while she's jogging. Rather than macing him like any sane person, she somehow charmed by him and says the only reason she won't date him is not that he's unattractive, broke, and generally has nothing going for him, but rather that she has to find someone for her "nottie" friend, June, who has also been around since the first grade, and the stakes are set.
In their quest to solve this problem, Nate and Arno will establish themselves to be truly loathsome individuals, but we're meant to ignore that because of the inherent nobility of first grade crushes.
If you've ever seen a rom-com, it won't be a spoiler to tell you that Nate encounters a rival who is everything he isn't: good looking, wealthy, athletic, charming, and talented. The thing is, this guy is also at least a good a person as Nate, probably better.
Anyway, yada, yada, you see the end coming a mile away, and we learn some valuable lessons about how important it is for women to be as attractive as possible if they ever want to be happy, and how important it is for men to, um...., have a pulse, I guess.
