Caleb has brown eyes, short, curly black hair, and dark skin. He wears a white and black T-shirt in Books 1 and 2. In Book 3, he wears a plaid shirt over a white T-shirt.
Caleb is an avid sports player who fits into the "golden boy"/popular sports guy stereotype. He is kind, honest, and patient.
You meet him in Book 1, Chapter 1 as Emma points out that she has a crush on him. He is nice, friendly and kind towards you and Emma. After he walks in on Zoe cheating on him with Brian he runs off. Your group runs after him and you can choose to talk to him privately on a cliff. You further develop your relationship later when he invites you to watch a movie with him and his friends.
He is kind and friendly to you when you first meet him, offering you help you around the school. You can hang out with him in the pool in Chapter 2. If you choose to comfort him at the cliff after he leaves the party you develop a stronger bond with him. You are close friends and work together to find a new quarterback for the football team. You can choose to go to the movies with Caleb, of which you will develop your relationship further.
Brian was Caleb's best friend, but he betrayed Caleb's trust by dating his girlfriend Zoe. Since Caleb discovered this, he and Brian are on hostile terms with each other.
Zoe is Caleb's ex-girlfriend. You catch Zoe cheating on Caleb with his then best friend Brian in a bathroom at Brian's house. If you choose to warn Caleb beforehand, he will like you. If you choose not to warn him, he will admonish you.
Emma had a crush on Caleb, and she finally asks him on a date in Book 1, Chapter 4. However, the next chapter reveals that he refuses and tells her he doesn't reciprocate her feelings because of the recent breakup with Zoe. If your character has been flirting with him, he also implies that his feelings for you are what's stopping him. Emma is saddened by his reaction, but they soon start talking again, as Caleb has made it clear that he still wants to be friends with her.
Ezra is Caleb's older brother. They are very different, but they respect each other's differences and are close nonetheless. However, their relationship took a turn for the worse when Ezra, a member of the band, supported Hearst High during a basketball match because of Principal Isa favoring the basketball team, of which Caleb is a member of, over other clubs.
Given their clashing interests and personalities, Caleb and Michael don't start off on the best of terms, worsened by Michael's refusal to join the football team as a QB after Brian leaves for Hearst. Their relationship builds however after Michael finally agrees to join the football team. In Book 2, Chapter 1, Caleb tries to convince Michael to join the basketball team too, but Michael kindly refuses, at which point Caleb admits that Michael is particularly bad at the sport anyway.
If Your Character does not go to homecoming with Caleb, he will go with Maria. When asked if they have a burgeoning relationship, they will try and say they are just going as friends. Maria states that she feels awkward after appearing taller than Caleb in 5 inch heels. Nevertheless, they enjoy the night together.
Jade is a love interest for Caleb (if he's single). He will show an attraction to her in Book 3, Chapter 3. A premium option in Chapter 8 allows you to send Caleb to a baseball game with Jade and improve their relationship together. Another premium option will get him to admit his feelings for her.
- Caleb is shown on the cover of High School Story, Book 1 and High School Story, Book 2.
- He has a severe allergy to pet fur, so he and Ezra have a pet goldfish named Rover.
- He resembles actor Jacob Artist.
- He shares the same forename as Caleb, a character from the Hero series.
- His toy car resembles a 1970 Chevrolet Chevelle SS.
- You can play as him in a premium scene of Book 3, Chapter 8, but only if he is not dating Your Character.