"Jake Dillinger is just a stereotypical jock with no personality"
Is a statement that will never fail to upset me. If you think this, I recommend rewatching Be More Chill.
(Warnings for talk of neglect, house fires, alcoholism, and underage drinking)
First of all, the entire point of Be More Chill is that the characters are stereotypes who deep down aren't what they seem to be. Yes, Rich is a stereotypical high school bully. But, he's actually being controlled by a SQUIP and is secretly nerdy and sweet and has his own set of issues.
This doesn't only apply to Rich. Every single character has this. The gossip girl, the queen bee, the stoner best friend, THE JOCK.
They are all high school stereotypes that have their own issues. Just because Jake doesn't have as much screen time as other characters does not mean it doesn't apply to him as well.
Within canon, Jake is abandoned by his parents because they're out of the country fleeing from their crimes. Jake participates in countless extracurriculars. Jake keeps himself busy with new things as often as possible. Jake feels lonely in his big house without his parents. Jake is tired of being the person that everyone thinks that he is.
All of these are explicitly stated in at least one of the three versions of Be More Chill.
Chloe's view of him: While a lot of Chloe's talk about Jake with Christine was jealously, there still is truth. Chloe has known Jake for a while and would use his issues against him (like when she specifically brought Jeremy into his parents' bedroom because she knew that would make Jake more upset than anything). When talking to Christine, she says Jake tries new things and doesn't always stick with them. I think this is an important thing to note. Also, Jake quits archery to be with Christine. I think that Jake enjoys sports and his clubs. But, I think it's less about him enjoying the activity and more about him trying desperately to occupy his mind.
The SQUIP even says this in Sync Up. I believe the line was, "This one participates in sports to avoid the feeling that deep down he will never be good enough." This line is so important to me because it confirms a lot of what the other lines and actions allude to. Sports and clubs are a way for Jake to get this rush of being loved and appreciated. He gets the pride of winning a game or leading a debate. Maybe he gets recognition from peers and teachers. When a child does not gain the affection and attention necessary from their parents, they look for it elsewhere. Acing tests and being good at basketball are the ways Jake can gain attention. They are the ways he can feel like he has done something worthy of pride. And maybe if it's good enough, his parents would look at him.
When asked if Jake had abandonment issues, Joe Tracz explained that there was a reason Jake felt like he had to be the best at everything all the time (referencing a line he says to Christine) This directly confirms what I am saying as well. Joe Tracz also said that Jake would be happy he had an excuse to leave that house after it burned down. I'm sure it was something that made Jake feel weighed down. His parents are gone. But, he still has their house. Sbarro was where they got pizza with him when he was a kid, so he continued to go there again and again. He is latching onto these reminders of his parents that I don't think he wants to latch on. He is stuck getting reminders of the things he has lost, and losing that house freed him in a way. If I'm remembering correctly, Joe Tracz said he was happy getting out of that house, and he got a new apartment near a Sbarro. I really like to envision this as Jake escapes what's holding him down and creates Sbarro into a positive thing that is more for him than it was a reminder of what he lost.
Jake's personality is something that would be modeled to gain attention. Neglected children often fall into the categories of acting out for attention and trying to be the best for affection. Jake would be the second option. He is a jock who does well in his classes because he craves the feeling of being good enough. If he is good enough, someone might love and care for him.
Jake does talk about his issues openly. Although, not in a venting way. And I think this is important to his character as well. When he brings up his parents being on the run, Christine says that it's really bad. "But the house is empty, so that's fun!" He is trying to pass his problems off as some cool, fun thing. Well, yeah, my parents are always out of the house. That means I can do what I want! I think, honestly, part of the reason he craved being with Christine is because she was the first person who really took his issues seriously. Instead of joking about throwing parties, she was concerned. When people talk about their issues in this light, a lot of the time, it's in hopes of being seen. I can't just talk about my feelings, but if I make a joke, maybe someone will notice and care. I think this is how Jake operates. But, when Christine notices, being the first to notice, he gets scared. He doesn't know how to be vulnerable. Neglected children are not good with emotional vulnerability and often do not know how to explain how they feel. Jake just tried to joke further.
When it comes to coping mechanisms, joking is one, but I don't think that's all. I think drinking and partying unfortunately became two things he gravitated towards. He mentions drinking on multiple occasions, and it would be an easy way to distract himself. Throwing parties would become a way to ruin the house and fill it with people. It's a big house and it is just him. Parties fill the house with people and erases his loneliness. Yet, his parents' room was off limits. He tries to maintain it. The room was the one thing he couldn't bring himself to ruin. The house can be ruined. He can ruin himself, trying to be perfect. He couldn't bring himself to touch that room. When the house burnt down, he didn't miss it. The house being gone gave him a freedom he didn't know he was searching for. He gets an apartment that was just for him. He was near his favorite restaurant that no longer just had to be about his parents and instead could be about him just simply liking their pizza. He was his own person who wasn't pretending to be someone he wasn't.
Jake is self-aware of his facade. "I'm tired of being the person that everyone thinks that I am." He does end up opening to Christine, despite being afraid earlier. I think it's interesting how he calls Christine out for not trying new things when he buries himself in new things to keep his brain occupied. She says his lonely, rich boy routine seems like an act. It isn't. It's his reality. Everyone thinks of him in a certain view and he can't escape it. Everyone thinks of him in these stereotypes of being a jock or rich boy or whatever. And he isn't that person. He's too deep in it to stop pretending. He's tired of it, anyway.
Jake being this rich boy jock may be true. It's just the way he's learned to protect himself and get the attention he needs. Because people need affection. It is a necessity. Jake isn't getting it any other way.
I do think that Jake can be a jerk and a bad person at times. I think that rings true for a lot of human beings. He is a hurting teenager, and a lot of hurting teenagers are assholes. I don't think he should be fully justified in every action he makes. However, I think there is a lot more to understand about him that people don't care to understand because he's a more minor character.
Jake is an asshole jock. The thing is, he is this more because he feels like he has to be than just because he likes being that way.
Jake is a complex character who deserves more recognition and understanding for being that way.