Cary is the one who first finds out about Kalinda's one-night stand with former State's Attorney Peter Florrick, but does not tell anyone about it.
After Childs is defeated by Peter for State's Attorney, Cary finds himself worried for his job (again) due to his strained relationship with Peter's wife Alicia, but after meeting with Peter the two men instantly hit it off, and Peter decides to retain Cary.
He then kisses her, telling her, "Welcome back to normal." In "Silly Season", Cary tells Kalinda of the fact that Childs is trying to investigate her.
He discovers her secret one-night stand with Peter Florrick in "Wrongful Termination", but keeps it a secret.
In "Conjugal" Cary first revealed a fascination in her. Kalinda, however, resisted all Cary's moves in the first two seasons.
In "Lifeguard", Kalinda famously tells Cary they're different as Spaghetti and Hydrogen. In "Great Firewall", after inquiring about why she told him about her new place, Kalinda tells him it "seemed normal".
As his character develops, however, Cary shows he actually has a lot to offer.
While he continues to compete with Alicia for a second-year associate position (as only one of them will ultimately be kept), he proves that he is a very capable lawyer, both adept at research and eager to learn.
His bail gets paid for by Bishop's lieutenant but the money gets revoked.
Like Alicia, Cary is a new first-year associate at the law firm in 2009.
At first, he comes across as a passive-aggressive foil for the show's main character.
Cary leaves Lockhart/Gardner or LG to start his own firm (Florrick/Agos) with all the fourth year associates and Alicia.
Will goes on a war path trying to destroy their firm.