It is never made clear how much older than Zach, Shaun is supposed to be. At the time setting of the film, Zach is supposed to be 22 and we can assume Shaun is probably no older than 30 -- probably 28 or 29. Zach and Gabe were friends in high school and someone in Gabe's family, probably his father, made the home video of him and Zach skateboarding. At this time Shaun is in his early to mid 20s and is finished with college and probably living it up in his apartment in L.A. and writing his first book.
When Shaun and Zach meet in the backyard of Shaun's home, it is clear they knew each other before Shaun left home for college. He well may have been attracted to Zach even then but knew better than to make a pass at a 16 or 17 year old boy. However, Zach at that age must already have been aware of certain urges that he did not yet fully understand and certainly would not admit even to himself. Hence, his ongoing relationship with Tori that probably started when they were still in high school.
Later, Shaun asks Zach about his sister Jeanne and her son Cody. "Cody must be getting big." So Shaun probably knew Jeanne and Zach when Cody was an infant. When Zach and Shaun go the beach party, Shaun sees Zach's girl friend, Tori, and says, "Yeah, I remember you."
In a later conversation when Shaun tells Zach that he is writing a second book but is having trouble with it, Zach tells him he read and liked his first book. Shaun asks, "You read it?" Zach replies, "Who knew there was so much drama inside the gates of "Pacific Bluffs"? I never knew." This suggests Zach realized the book was semi-autobiographical, "You changed a few names." Shaun says, "I never knew you knew about me." Shaun is in fact saying that he didn't realize that Zach knew that he was gay. At this point Zach looks just a bit flustered and looks away as they are walking together and changes the subject. Shaun has, in fact, opened the door to Zach and although he is not sure how Zach feels about him, he is certainly becoming attracted to Zach.
In the commentary track, Brad Rowe says: "Character Shaun is doing his best to hide the fact that he has great lust going just now."
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