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Poor Tobias. The boy is cast as someone who, given his status in Dauntless, should be almost fearless (his nickname, "Four," is the number of fears he has), yet he has to play the pawn to both of his parents, who are each on opposite sides of the city's struggle for power. Even when he becomes a leader of Dauntless, he's only doing so at the insistence of his mother, Evelyn, who wants to demolish the factions and take control of the city herself.
As a result, Tobias can be a little… how do we say this tactfully?… inept. This is especially true when it comes to his dealings with women. His relationship with Tris, for one, is pretty dicey. He wants to be the man in the relationship, employing the "touch[ing] the small of [Tris's] back" (2.73) maneuver as if she has an invisible steering wheel there to guide her where he wants her to go.
Basically, Tobias doesn't let Tris have any sort of agency in the relationship. Remember that time he took Tris to a meeting with Evelyn? He took her because she's good at reading situations. Yet when she tells him her instinctual reaction, he shoots her down. This disagreement sets the endgame of the novel into motion and pretty much brings down the entire faction system—something that probably wouldn't have happened if he had trusted Tris's instincts.
Of course, we have to ask: is bringing down the faction system a good thing? Perhaps he made the right decision, and not just the one that sets us up for a sequel. It's hard to tell, though, because Tobias's decisions seem to be motivated by fear (and by random chips on his shoulder) more than anything else.
Tobias's inferiority complex is worsened by two things. 1) Everyone in the cafeteria calls him a "coward" (20.7), proving that no, we're not over all this high school drama, even in a post-apocalyptic society; and 2) Tris treats him like a boy.
Tris even says to him, "How is it I know this little about the boy who says he loves me—the boy whose real name is powerful enough to keep us alive in a train car full of enemies?" (8.66). Tris's habit viewing her boyfriend as just a boy does nothing for his self-esteem. (Plus, how is it that Tris, who bristles at being called "little girl," thinks it's okay to call Tobias a "boy"?)
Whatever he thinks of himself, the reality is that Tobias is a boy who is defined at least partly by his fears. It's in his very nickname, and his every reaction is made toward overcoming these fears. Fear of heights. Fear of his father. And fear of losing Tris, the girl whom he loves although, honestly, we sometimes can't figure out why.
Do you think Tobias will become a man of his own, separate from both his parents and Tris? Can he truly grow with all these people in his life trying to control him?