Stewart is a bright kid, perhaps even a genius. His dad has begun dating again after the death of Stewart's mother, and he's getting pretty serious with Ashley's mom. Ashley is something of an all-American girl, but she's not nearly as sharp as Stewart. As if it weren't weird enough that their parents were dating, the two are forced to move in together when their parents move in together. The popular girl and the awkward nerd are suddenly would-be siblings, against their will.
Although Ashley despises Stewart for his awkwardness, she cannot help but feel sorry for him when he mourns his lost mother. In that respect, Stewart is truly suffering, inconsolably. In light of this, Ashley's distaste begins to feel unneeded. In addition, Stewart learns that the real reason Ashley's father left is because he is gay. Ashley is mourning that loss while simultaneously trying to figure out how she feels about her father's sexual orientation.
When Ashley finally begins to date again, she picks Jared. Stewart knows from personal experience that Jared is not a good guy, but Ashley chalks it up to Stewart's bad social skills, but she can't help but notice red flags. Ultimately, Ashley realizes that Stewart was right about Jared, and the two realize that they have accidentally formed an unlikely yet formidable friendship.
