Ray is the oldest and most mature member of the skate crew, serving as a kind of unofficial leader and older-brother figure to the others. He is a talented skateboarder with a laid-back, thoughtful personality and an unusually reflective way of looking at life. Unlike some of the other boys, Ray doesn't seem as interested in proving how tough or reckless he is. He has a natural confidence that comes from being comfortable with himself and his abilities. Ray is observant and often notices things that the others overlook. He understands that the younger kids in the group, particularly Stevie, are looking up to him, which makes him more responsible than the others. Although he can joke around and participate in the group's antics, he is generally the one who brings a calmer energy to the group. He has a strong sense of loyalty toward his friends and genuinely cares about them. His skateboarding is extremely important to him, and he takes the craft seriously. Ray represents the possibility of growing up without completely losing the freedom and excitement of being young. He becomes one of Stevie's biggest influences because Stevie sees him as the kind of older teenager he wants to become. Ray isn't perfect, though; he has his own frustrations and personal problems, and his maturity doesn't prevent him from making mistakes.

Ruben is one of the younger members of the skate crew and is energetic, competitive, and eager to establish himself among the older skaters. He is loud and sometimes obnoxious, but much of this comes from wanting to be taken seriously. He wants to fit in and doesn't want the others to see him as weak or inexperienced. Ruben can be particularly teasing toward Stevie. Since Stevie is younger and inexperienced, Ruben sometimes treats him as an easy target for jokes and challenges. Their interactions have a competitive quality, with both boys wanting approval from the older members of the group. Despite his rougher attitude, Ruben isn't simply mean. He is still a kid trying to figure out his place within a group where everyone has different personalities and levels of experience. He can be impulsive and easily caught up in whatever the group is doing. His personality reflects the way young teenagers can imitate the older people around them while still having a lot of growing up to do. Ruben's friendship with the group is centered around skateboarding, joking around, hanging out in the streets, and trying to look cooler and older than they actually are. His competitive nature gives the group some of its playful tension.

Fourth Grade is one of the more distinctive personalities in the group. His nickname immediately gives him a goofy, slightly ridiculous quality, and he has an eccentric sense of humor that helps make him stand out. He is part of the older-skater crowd Stevie desperately wants to join, making him another person Stevie watches closely and tries to imitate. Fourth Grade has a carefree attitude and tends to go along with the group's behavior rather than taking things particularly seriously. He enjoys joking around and contributing to the chaotic atmosphere surrounding the skaters. Compared with Ray's thoughtful personality, Fourth Grade is much more immature and impulsive. He represents the fun and ridiculous side of the skateboarding group. Hanging out with him isn't necessarily about having deep conversations or carefully planned activities; it's about being outside, skating, laughing, messing around, and seeing what happens. His personality makes the group feel like a genuine collection of teenagers rather than a perfectly organized friend group. Fourth Grade also contributes to Stevie's fascination with the older skaters. To Stevie, these boys seem independent and exciting because they have their own world that exists outside of school and family. Fourth Grade is part of that world, and Stevie wants desperately to prove that he belongs in it.

Fcksit is one of the more energetic and unpredictable members of the skate crew in Mid90s. He has a loud, confident personality and often acts like he doesn't take anything too seriously. He enjoys making his friends laugh, showing off, and turning ordinary moments into something entertaining. His carefree attitude makes him seem incredibly cool to Stevie, who looks up to the older skaters and wants to fit in with them. He has a rebellious sense of humor and likes being the center of attention. He's the type of person who might make a ridiculous comment, start teasing someone, or turn a simple conversation into a joke. He can be immature and impulsive, but that's also part of what makes him memorable within the group. Around the other skaters, he is comfortable being himself and doesn't seem particularly concerned with how others perceive him. He has a strong presence and can easily influence the mood of the group. His friendship with the others is based largely around skating, hanging out, joking around, and sharing the carefree atmosphere of their teenage years. Although he acts confident, he is still a teenager figuring himself out. His personality reflects the messy, awkward, and sometimes funny process of trying to seem older while still growing up. For Stevie, he represents the exciting side of the older kids' world, making him someone Stevie naturally finds fascinating.