When the fact that a girl is incredibly hot is overshadowed by her fervent Christianity. Even though you would love to have sex with her, her religiosity is so overpowering that you would much rather just talk some sense into her.
This makes a reference to Russell's teapot, a thought experiment meant to demonstrate that non-belief in religion is the rational choice.
Man, Caitlin is so hot, I would totally hit it... hit it over the head with Russell's teapot, that is.
sh-he-it (pronoun) pronounced "shee-yit" -- 1. a generic pronoun, referring to a person of unknown or indeterminate gender, 2. a "politically correct" pronoun used to avoid identifying gender in hopes that the pronoun will not offend males, females, or any of the myriad other gender identities.
Bob is so conventional. Sh-he-it doesn't realize that using pronouns like "he" and "she" is offensive to people who are sensitive to gender labels.